3-(Morpholin-4-yl)propanoic acid → (3aR,4S,7aR)-4-(3-morpholin-4-yl-propionyloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

HRID 2176753

Reaction equation

HRID 2176753 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].[N:24]1([CH2:30][CH2:31][C:32](O)=[O:33])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[CH3:1][O:2][C:3]([N:5]1[C@H:13]2[C@H:8]([C@:9]([O:23][C:32](=[O:33])[CH2:31][CH2:30][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)([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 4108133-(Morpholin-4-yl)propanoic acidHCID 68276168(3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester

Product 1

HCID 60142172(3aR,4S,7aR)-4-(3-morpholin-4-yl-propionyloxy)-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 3-morpholin-4-yl-propionic acid to yield (3aR,4S,7aR)-4-(3-morpholin-4-yl-propionyloxy)-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester. MS [M+H]=296 (ester elimination ion); RT=4.088 min; LC-MS Method III

Sources & evidence

ORD record
ord-ae0c7bffba2b45b6a176912e70e34509
Source dataset
uspto-grants-2015_06
Patent number
US09067881B2

Linked notes

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