Triethylamine → Perhydro-l-pyrrolizinyl methanesulfonate
Reaction equation
[CH:1]1([OH:9])[CH:8]2[N:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].[Cl-].[NH4+].[Na]>ClCCl>[CH3:17][S:18]([O:9][CH:1]1[CH:8]2[N:4]([CH2:5][CH2:6][CH2:7]2)[CH2:3][CH2:2]1)(=[O:20])=[O:19]Participants
Conditions
- Temperature
- 0 °C
Procedure
A mixture of perhydro-1-pyrrolizinol (0.5 g, 3.94 mmol) and triethylamine (0.60 g, 5.91 mmol) in dichloromethane (10 ml) was stirred at 0° C. under an atmosphere of nitrogen. Methanesulfonyl chloride (0.68 g, 5.91 mmol) was added, then the mixture was allowed to warm to ambient temperature and stirred for 8 hours. Saturated aqueous ammonium chloride (10 ml), dichloromethane (25 ml) and saturated aqueous sodium bicarboante (10 ml) were added. The organic layer was dried over magnesium sulfate filtered and the filtrate evaporated under reduced pressure to give a residue. Purification of the material by flash chromatography on silica gel using heptane/ethyl acetate (1:3) as an eluent yielded perhydro-l-pyrrolizinyl methanesulfonate (0.54 g): 1H NMR (DMSO-d6, 400 MHz) δ 4.96 (m, 1H), 3.61 (m, 1H), 2.9-3.3 (m, 6H), 2.35 (m, 1H), 1.55-2.25 (m, 6H).
Workup
- temperatureto warm to ambient temperature
- stirringstirred for 8 hours
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customthe filtrate evaporated under reduced pressure
- customto give a residue
- customPurification of the material by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-3d9f1a17265e42898567545c2cce11d4
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06713474B2
Reaction notes
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