1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 67025925, compound

HRID 1951141Notes

Reaction equation

HRID 1951141 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([C@@H:10]2[C@@H:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:13][NH:12][CH2:11]2)[CH3:9])=[O:7])=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41](O)=[O:42])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41]([N:12]2[CH2:11][CH:10]([N:8]([C:6](=[O:7])[C:5]3[CH:22]=[CH:23][C:2]([Cl:1])=[C:3]([C:24]([F:27])([F:26])[F:25])[CH:4]=3)[CH3:9])[CH:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:13]2)=[O:42])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

3

Reactant 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 67025840HCID 67025840, compound

Product 1

HCID 67025925HCID 67025925, compound

Procedure

In analogy to the procedure described for the synthesis of example 97, the title compound 4-{(3SR,4RS)-3-(4-chloro-phenyl)-4-[(4-chloro-3-trifluoromethyl-benzoyl)-methyl-amino]-pyrrolidine-1-carbonyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 4-chloro-N-[(3R,4S)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-N-methyl-3-trifluoromethyl-benzamide instead of {4-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone using piperidine-1,4-dicarboxylic acid mono-tert-butyl ester instead of 4-chloro-3-(trifluoromethyl)benzoic acid and was obtained as a white foam. MS m/e: 528.2 [M-BOC]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 97
  2. customwas obtained as a white foam

Sources & evidence

ORD record
ord-f1e934c789c145f19d737299936b519c
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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