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

HRID 2167782Notes

Reaction equation

HRID 2167782 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-a4f23f0eac064becb620957e8fa1e220
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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