1-(Cyclopropylmethyl)piperidine-4-carboxylic acid → rac-[(3R,4S)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

HRID 587312Notes

Reaction equation

HRID 587312 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([C@@H:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:23]1([CH2:26][N:27]2[CH2:32][CH2:31][CH:30]([C:33](O)=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24]1>>[C:1]([O:5][C:6](=[O:22])[N:7]([C@@H:9]1[C@@H:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:12][N:11]([C:33]([CH:30]2[CH2:31][CH2:32][N:27]([CH2:26][CH:23]3[CH2:25][CH2:24]3)[CH2:28][CH2:29]2)=[O:34])[CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 162440151-(Cyclopropylmethyl)piperidine-4-carboxylic acidHCID 58009331Rel-tert-butyl ((3R,4S)-4-(3,4-dichlorophenyl)pyrrolidin-3-yl)(methyl)carbamate

Product 1

HCID 58009221rac-[(3R,4S)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Procedure

In analogy to the procedure described for the synthesis of example 1 (step f), the title compound rac-[(3R,4S)-1-(1-cyclopropylmethyl-piperidine-4-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester was prepared from rac-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester using 1-(1-cyclopropylmethyl)-piperidine-4-carboxylic acid instead of 1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid and was obtained as a brown oil which was directly used in the next step without purification.

Workup

  1. customIn analogy to the procedure described for the synthesis of example 1 (step f)
  2. customwas obtained as a brown oil which
  3. customwas directly used in the next step without purification

Sources & evidence

ORD record
ord-3b3adfcb09b04baf9ed215cca95846f9
Source dataset
uspto-grants-2016_01
Patent number
US09226916B2

Reaction notes

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