Diisopropylethylamine → rac-[(3S,4R)-4-(3 4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester

HRID 1951077Notes

Reaction equation

HRID 1951077 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([C@H:10]1[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:13][NH:12][CH2:11]1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:33][S:34]([N:37]1[CH2:42][CH2:41][N:40]([C:43](Cl)=[O:44])[CH2:39][CH2:38]1)(=[O:36])=[O:35]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[N:7]([C@H:10]1[C@H:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:13][N:12]([C:43]([N:40]2[CH2:39][CH2:38][N:37]([S:34]([CH3:33])(=[O:36])=[O:35])[CH2:42][CH2:41]2)=[O:44])[CH2:11]1)[CH2:8][CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67025594Rac-[(3s,4r)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl esterHCID 798864701-Piperazinecarbonyl chloride, 4-(methylsulfonyl)-

Product 1

HCID 67026416rac-[(3S,4R)-4-(3 4-Dichloro-phenyl)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl esterYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-[(3S,4R)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-carbamic acid tert-butyl ester (0.25 g, 0.69 mmol) in CH2Cl2 (5 ml) was added ethyl-diisopropyl-amine (0.20 ml, 1.1 mmol) and 4-methanesulfonyl-piperazine-1-carbonyl chloride (189 mg, 0.83 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc) afforded 0.37 g (97%) of the title compound as a white solid. ES-MS m/e: 549.3 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-24793f48807642adb391763dbdefd298
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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