Triethylamine → (1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate
Reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl.O>[CH3:22][S:23]([O:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:3]1)(=[O:25])=[O:24]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 2.5 °C
Procedure
To a solution of tert-butyl N-[(1S,3R)-3-hydroxycyclopentyl]carbamate (3.0 g, 14.91 mmol, 1.00 equiv) and triethylamine (3.0 g, 29.65 mmol, 1.99 equiv) in dichloromethane (50 mL) was added methanesulfonyl chloride (2.2 g, 19.21 mmol, 1.29 equiv) dropwise with stirring at 0-5° C. After addition was completed, the reaction mixture was warmed to room temperature and stirred at room temperature for 2 h. The mixture was diluted with 50 mL of water and extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 2×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.8 g (91%) of tert-butyl N-[(1S,3R)-3-(methane sulfonyloxy)cyclopentyl]carbamate as a white solid.
Workup
- additionAfter addition
- temperaturethe reaction mixture was warmed to room temperature
- stirringstirred at room temperature for 2 h
- extractionextracted with 2×50 mL of ethyl acetate
- washThe combined organic layers was washed with 2×30 mL of brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-e3024cdeed0f42fc8a77e93bdc382fcd
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296732B2
Reaction notes
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