1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 58303108, compound

HRID 587333Notes

Reaction equation

HRID 587333 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:25])[N:10]([C@@H:12]2[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([C:39](O)=[O:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([C:39]([N:14]2[CH2:13][C@H:12]([N:10]([C:9]([O:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:25])[CH3:11])[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15]2)=[O:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 67234230rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester

Product 1

HCID 58303108HCID 58303108, compound

Procedure

In analogy to the procedure described for the synthesis of example 44 (step c), the title compound rac-4-{(3S,4R)-3-(3,4-dichloro-phenyl)-4-[(4-fluoro-phenoxycarbonyl)-methyl-amino]-pyrrolidine-1-carbonyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester using piperidine-1,4-dicarboxylic acid mono-tert-butyl ester instead of 1-methylcyclopropane-1-carboxylic acid and was obtained as a yellow foam. MS m/e: 593.1 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 44 (step c)
  2. customwas obtained as a yellow foam

Sources & evidence

ORD record
ord-da611b993f6e460e9ddc8e2529992340
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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