Triethylamine → Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)(=[O:28])=[O:27]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To benzyl 4-hydroxypiperidine-1-carboxylate (48.8 g, 207 mmol) in CH2Cl2 (400 mL) was added triethylamine (57.8 mL, 415 mmol), the mixture was cooled to 0° C. under nitrogen and then methanesulfonyl chloride (17.78 mL, 228 mmol) was added over 15 minutes keeping internal temperature below 30° C. After 2 hours at 0° C., the reaction was quenched with 300 mL of 0.1 N aqueous HCl, the organic layer was washed with 300 mL of water, 300 mL of brine, dried with MgSO4, filtered and concentrated to give the product (69.5 g) as an amber liquid which was used without further purification. MS (ESI) 314.4 (M+1).
Workup
- customtemperature below 30° C
- customthe reaction was quenched with 300 mL of 0.1 N aqueous HCl
- washthe organic layer was washed with 300 mL of water, 300 mL of brine
- dry with materialdried with MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-30a755737cd34cb69f195dcada56be77
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513424B2
Reaction notes
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