Diisopropylethylamine → Rac-[(3s,4r)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester

HRID 1951072Notes

Reaction equation

HRID 1951072 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:31][S:32]([N:35]1[CH2:40][CH2:39][N:38]([C:41](Cl)=[O:42])[CH2:37][CH2:36]1)(=[O:34])=[O:33]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][N:11]([C:41]([N:38]2[CH2:37][CH2:36][N:35]([S:32]([CH3:31])(=[O:34])=[O:33])[CH2:40][CH2:39]2)=[O:42])[CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67025587rel-tert-Butyl ((3S,4R)-4-(4-chlorophenyl)pyrrolidin-3-yl)(methyl)carbamateHCID 798864701-Piperazinecarbonyl chloride, 4-(methylsulfonyl)-

Product 1

HCID 67026258Rac-[(3s,4r)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl esterYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-[(3S,4R)-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (0.76 g, 2.46 mmol) in CH2Cl2 (10 ml) was added ethyl-diisopropyl-amine (0.51 ml, 2.95 mmol) and 4-methanesulfonyl-piperazine-1-carbonyl chloride (0.61 g, 2.7 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/Hx 1:1) afforded 0.87 g (70%) of the title compound as a white solid. ES-MS m/e: 501.4 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-19362d6ef2524c64816428803127f8bd
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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