Triethylamine → (2S,4S)-2-Methanesulfonyloxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 238988Notes

Reaction equation

HRID 238988 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]1[CH2:19][OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:10][C@H:9]1[CH2:19][O:20][S:29]([CH3:28])(=[O:31])=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58002916(2S,4S)-2-Hydroxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58002926(2S,4S)-2-Methanesulfonyloxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 106.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2.5 g of (2S,4S)-2-Hydroxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester (9.01 mmol) in 70 ml dichloromethane were added 1.92 g of triethylamine (18.02 mmol) and 1.03 g of methanesulfonylchloride (9.01 mmol), dissolved in 5 ml dichloromethane. The reaction was stirred for 16 h at room temperature and yielded 3.4 g of product after standard workup.

Sources & evidence

ORD record
ord-d5475ab031a6407187143e3f2badc528
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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