Methanesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 1804591Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:15][S:16]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (550 mg, 2.5 mmol) and DMAP (296 mg, 2.5 mmol) in dichloromethane (15 mL) cooled to 0° C. by ice/water bath was added methanesulfonylchloride (189 μL, 2.5 mmol) and the resulting mixture stirred for 10 min at 0° C. and then for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×30 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under vacuum. The residue oil was purified via silica gel preparative plates (3×1000 mM) eluting with 50% ethyl acetate in hexane to afford the title compound (555 mg, 89%). ESI-MS calculated for C11H21NO5S: Exact Mass: 279.11. Found 302.13 (MNa)+.

Workup

waitfor an additional hour at RT
customThe mixture was quenched with ice water
extractionextracted with ethyl acetate (2×30 mL)
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue oil was purified via silica gel preparative plates (3×1000 mM)
washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-bd4e878e14464faf9dc5d87fbfa63096
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354403B2

Reaction notes

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