Triethylamine → Tert-butyl 3-(methanesulfonyloxy)pyrrolidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 50 ml round-bottomed flask, 3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (300 mg, 1.6 mmol) was dissolved in dichloromethane 912 ml). The colorless solution was cooled to 0° C. and triethylamine (0.34 ml, 2.44 mmol) and methanesulfonyl chloride (0.14 ml, 1.8 mmol) were added. The reaction mixture was stirred at 0° C. for 1.5 h then quenched with water and extracted with dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil which was used without further purification.
Workup
- customthen quenched with water
- extractionextracted with dichloromethane (2×)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5d49a29682914acf8ea99426eec26dd5
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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