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

HRID 1951067Notes

Reaction equation

HRID 1951067 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH3:19])[C@H:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:30][S:31]([N:34]1[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]1)(=[O:33])=[O:32]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][N:10]([C:40]([N:37]2[CH2:36][CH2:35][N:34]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:39][CH2:38]2)=[O:41])[CH2:9]1)[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67025570Rac-methyl-((3s,4r)-4-phenyl-pyrrolidin-3-yl)-carbamic acid tert-butyl esterHCID 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 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-methyl-((3S,4R)-4-phenyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (0.57 g, 2.1 mmol) in CH2Cl2 (15 ml) was added ethyl-diisopropyl-amine (0.53 ml, 3.11 mmol) and 4-methanesulfonyl-piperazine-1-carbonyl chloride (0.56 g, 2.5 mmol). Stirring was continued over night at RT, concentrated under vacuo and purification by flash chromatography (SiO2, EtOAc/Hx 1:1) afforded 0.64 g (66%) of rac-[(3S,4R)-1-(4-methanesulfonyl-piperazine-1-carbonyl)-4-phenyl-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester as a white solid. ES-MS m/e: 467.3 (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-8f4945cbc82245d9a3dcf104c50d4348
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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