Phenelzine → (2S,4R)-4-Cyclopropylmethanesulfonyl-1-(5-methyl-2-phenethyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697754

Reaction equation

HRID 1697754 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17](=S)[CH2:18][C:19](=O)[CH3:20])=[O:4].[C:23]1([CH2:29][CH2:30][NH:31][NH2:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([CH2:13][CH:14]2[CH2:16][CH2:15]2)(=[O:12])=[O:11])[CH2:7][N:6]1[C:17]1[N:31]([CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:32]=[C:19]([CH3:20])[CH:18]=1)=[O:4]

Participants

3

Reactant 2

HCID 3675PhenelzineHCID 86646864(2S,4R)-4-Cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Product 1

HCID 67278218(2S,4R)-4-Cyclopropylmethanesulfonyl-1-(5-methyl-2-phenethyl-2H-pyrazol-3-yl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester (example 445c) was reacted with 1-(2-phenylethyl)hydrazine (CAS Reg. No. 51-71-8) to give the title compound as brown solid. MS (ESI): m/z=432.6 [M+H]+.

Sources & evidence

ORD record
ord-dd1d37cdf4f343aab6f505ebcd8fe6e7
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Linked notes

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