Triethylamine → 1,1-Dimethylethyl (2R)-2-[[(methylsulfonyl)oxy]methyl]-1-pyrrolidinecarboxylate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([N:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[CH2:18][OH:19])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:19][CH2:18][C@H:14]1[CH2:15][CH2:16][CH2:17][N:13]1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:4])=[O:3]Participants
5
Procedure
Methanesulfonyl chloride (0.06 mL, 0.77 mmol) was added to a solution of (R)-N-Boc-pyrrolidine-2-methanol (125.3 mg, 0.62 mmol) and triethylamine (0.22 mL, 1.6 mmol) in dichloromethane at 0° C. under argon. After stirring for 1 h, the reaction mixture was partitioned between dichloromethane (50 mL) and sodium hydrogen sulfate (15 mL). The organic layer was sequentially washed with water (15 mL) and brine (15 mL), dried over anhydrous sodium sulfate and the solvent was removed in vacuo to yield (R)-N-Boc-pyrrolidine-2-methanol methanesulfonate, which was used crude.
Workup
- customthe reaction mixture was partitioned between dichloromethane (50 mL) and sodium hydrogen sulfate (15 mL)
- washThe organic layer was sequentially washed with water (15 mL) and brine (15 mL)
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-44a4dd90380b46fe9dfcf308ca52e882
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380242B1
Reaction notes
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