Triethylamine → 1,1-Dimethylethyl N-[(3S)-1-(methylsulfonyl)-3-pyrrolidinyl]carbamate

HRID 926719Notes

Reaction equation

HRID 926719 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([N:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:7]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 589598791,1-Dimethylethyl N-[(3S)-1-(methylsulfonyl)-3-pyrrolidinyl]carbamateYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methane sulfonyl chloride (204 mg, 1.78 mmol) was added to a solution of (S)-tert-butyl pyrrolidin-3-ylcarbamate (300 mg, 1.62 mmol) and Et3N (197 mg, 1.94 mmol) in DCM (6 mL) at 0-5° C.; stirring was continued at 20-35° C. for 2 h. The reaction mixture was diluted with DCM, washed with water, aqueous NaHCO3 solution followed by brine to afford 250 mg of the title compound.

Workup

  1. washwashed with water, aqueous NaHCO3 solution

Sources & evidence

ORD record
ord-cb59217d36284eafb639bcaa1a0fd602
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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