Triethylamine → Rac-[(3s,4r)-1-(4-cyano-benzoyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

HRID 1951079Notes

Reaction equation

HRID 1951079 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].C(N(CC)CC)C.[C:30]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)#[N:31]>C(Cl)Cl>[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:36](=[O:37])[C:35]2[CH:39]=[CH:40][C:32]([C:30]#[N:31])=[CH:33][CH:34]=2)[CH2:10]1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 67025568Rac-[(3s,4r)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 67025575Rac-[(3s,4r)-1-(4-cyano-benzoyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (810 mg, 2.35 mmol, described herein above) in CH2Cl2 (20 ml) was added triethyl-amine (0.42 ml, 3.05 mmol) and 4-cyano-benzoyl chloride (466 mg, 2.81 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/Hx 2:1) afforded 1.09 g (98%) of the title compound as a white foam. ES-MS m/e: 474.4 (M+H+).

Workup

  1. waitwas continued over night at RT
  2. concentrationconcentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/Hx 2:1)

Sources & evidence

ORD record
ord-e5c4802c278645b8972f9094088d555e
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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