rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester → HCID 178485977, compound

HRID 587325Notes

Reaction equation

HRID 587325 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.[OH:26][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33](O)=[O:34])[CH2:29][CH2:28]1>>[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][N:14]([C:33]([C@H:30]3[CH2:31][CH2:32][C@H:27]([OH:26])[CH2:28][CH2:29]3)=[O:34])[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 67234230rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl esterHCID 178525780HCID 178525780, compound

Product 1

HCID 178485977HCID 178485977, compound

Procedure

In analogy to the procedure described for the synthesis of example 1 (step f), the title compound rac-[(3R,4S)-4-(3,4-Dichloro-phenyl)-1-(trans-4-hydroxy-cyclohexanecarbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester was prepared from rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester instead of rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester using trans-4-hydroxycyclohexanecarboxylic acid instead of 1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid and was obtained as a light brown oil. MS m/e: 509.3 [M]+.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 1 (step f)
  2. customwas obtained as a light brown oil

Sources & evidence

ORD record
ord-0e1d8a3efabc47198d4f46ff78dc6cdb
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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