GB927808A - Production of nor-tropanol derivatives - Google Patents
Production of nor-tropanol derivativesInfo
- Publication number
- GB927808A GB927808A GB36984/60A GB3698460A GB927808A GB 927808 A GB927808 A GB 927808A GB 36984/60 A GB36984/60 A GB 36984/60A GB 3698460 A GB3698460 A GB 3698460A GB 927808 A GB927808 A GB 927808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nortropan
- benzyl
- benzoyl
- derivatives
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- YEASGSCSOSLILK-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octan-5-ol Chemical class C1CCC2CCC1(O)N2 YEASGSCSOSLILK-UHFFFAOYSA-N 0.000 title 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- -1 benzoic acid halide Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-benzyl derivatives of nortropan-3a - or 3b -ol are produced by a process in which the carbonyl group of the amide grouping of an N-benzoyl nortropan-3a - or 3b -ol or an ester thereof is reduced with a metal hydride reducing agent to a methylene group, the N-benzyl and N-benzoyl groups being unsubstituted or substituted in the nucleus with a halogen atom or an alkyl, aryl or aralkyl group. The preferred reducing agent is lithium aluminium hydride or sodium borohydride. The N-benzoyl compound used as starting material may be prepared by the reaction of a nortropan-3a - or 3b -ol or an ester thereof with a benzoylating agent, such as a benzoic acid halide, in the presence of a base. In the examples the preparation of (a) N-benzyl nortropan-3a -ol, (b) N-p-chlorobenzyl nortropan-3a -ol, and (c) N-benzyl nortropan-3b -ol is described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE000911 | 1959-11-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB927808A true GB927808A (en) | 1963-06-06 |
Family
ID=10995147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36984/60A Expired GB927808A (en) | 1959-11-19 | 1960-10-27 | Production of nor-tropanol derivatives |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT227386B (en) |
| GB (1) | GB927808A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113846133A (en) * | 2021-10-21 | 2021-12-28 | 大连万福制药有限公司 | Method for preparing tropine through biological enzyme catalysis |
-
1960
- 1960-10-14 AT AT774260A patent/AT227386B/en active
- 1960-10-27 GB GB36984/60A patent/GB927808A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113846133A (en) * | 2021-10-21 | 2021-12-28 | 大连万福制药有限公司 | Method for preparing tropine through biological enzyme catalysis |
Also Published As
| Publication number | Publication date |
|---|---|
| AT227386B (en) | 1963-05-10 |
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