1,2-Pyrrolidinedicarboxylic acid, 4-cyano-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)- → 4-Cyano-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

HRID 417620Notes

Reaction equation

HRID 417620 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([Br:29])[CH:25]=2)[CH:20]=1)=[O:18])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].COC(=O)[C@@H:33]1C[C@H](C#N)C[N:34]1C(OC(C)(C)C)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:33]#[N:34])[CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([Br:29])[CH:25]=2)[CH:20]=1)=[O:18])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 177504541,2-Pyrrolidinedicarboxylic acid, 4-cyano-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-HCID 66620206Pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

Product 1

HCID 666204204-Cyano-pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

Procedure

Title compound was prepared according to the method employed to prepare pyrrolidine-1,2-dicarboxylic acid 2-[2-(6-bromo-naphthalen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester in Example CL, substituting pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester with N-Boc-cis-4-cyano-L-proline methyl ester (643 mg, 67%)

Sources & evidence

ORD record
ord-f3dedc2994f849a99fdef93d4905b6a3
Source dataset
uspto-grants-2012_01
Patent number
US08088368B2

Reaction notes

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