Water → 1,1-Dimethylethyl 4-Hydroxymethyl-4-methanesulfonyloxymethyl-1-piperidinecarboxylate

HRID 2213012Notes

Reaction equation

HRID 2213012 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1([CH2:21][OH:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.C(N(CC)CC)C.O>ClCCl>[OH:6][CH2:7][C:8]1([CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21955203Tert-butyl 4,4-bis(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 179799801,1-Dimethylethyl 4-Hydroxymethyl-4-methanesulfonyloxymethyl-1-piperidinecarboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (44 μL, 0.56 mmol) in dichloromethane (10 mL) was added slowly to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4,4-bis(hydroxymethyl)-1-piperidinecarboxylate (Description 67, 140 mg, 0.56 mmol) and triethylamine (95 μL, 0.68 mmol) in dichloromethane (50 mL). The mixture was allowed to warm to room temperature and stirred for 16 hours. Water (10 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (2×40 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20 increasing to 0:100), to give the title compound (98 mg, 54%). m/z (ES+) 324 (M+1).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×40 mL)
  3. dry with materialthe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with isohexane/EtOAc (80:20 increasing to 0:100)

Sources & evidence

ORD record
ord-10610de2250b47a9a710fed64b01bc17
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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