N,N-Dimethylglycine → (3aR,4S,7aR)-4-(2-dimethylamino-acetoxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

HRID 2176734Notes

Reaction equation

HRID 2176734 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C@@H:13]2[C@@H:8]([C@@:9]([OH:23])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[CH3:24][N:25]([CH2:27][C:28](O)=[O:29])[CH3:26]>>[CH3:1][O:2][C:3]([N:5]1[C@H:13]2[C@H:8]([C@:9]([O:23][C:28](=[O:29])[CH2:27][N:25]([CH3:26])[CH3:24])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 60141604(3aR,4S,7aR)-4-(2-dimethylamino-acetoxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Procedure

Synthesis in analogy to the General Method 1 starting from (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester and dimethylamino acetic acid to yield (3aR,4S,7aR)-4-(2-dimethylamino-acetoxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester. MS [M+H] 296 (ester elimination ion); Rt 4.592 min; LC-MS Method II

Sources & evidence

ORD record
ord-cef8412708c247df82ab7b043efeeded
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Reaction notes

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