Piperidin-4-ol → 1-(3-((Phenylsulfonyl)methyl)oxetan-3-yl)piperidin-4-ol

HRID 921795Notes

Reaction equation

HRID 921795 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[C:8]1([S:14]([CH:17]=[C:18]2[CH2:21][O:20][CH2:19]2)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[C:8]1([S:14]([CH2:17][C:18]2([N:1]3[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]3)[CH2:21][O:20][CH2:19]2)(=[O:16])=[O:15])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 462038523-((Phenylsulfonyl)methylene)oxetane

Product 1

HCID 867086921-(3-((Phenylsulfonyl)methyl)oxetan-3-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of piperidin-4-ol (100 mg, 0.989 mmol) and 3-((phenylsulfonyl)methylene)oxetane (prepared according to a published literature procedure: Wuitschik et al. J. Med. Chem. 53(8) 3227-3246, 2010, 416 mg, 1.977 mmol) in methanol (5 mL) was heated at 50° C. for 20 h. Solvent was evaporated in vacuo and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 0-8% 2 N ammonia in methanol/dichloromethane). 1-(3-((phenylsulfonyl)methyl)oxetan-3-yl)piperidin-4-ol (300 mg) was obtained as a colorless oil.

Workup

  1. customSolvent was evaporated in vacuo
  2. customthe crude product was purified by flash chromatography on silica gel using
  3. washan automated ISCO system (40 g column, eluting with 0-8% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-06abf88058c24f9a9db721fb33e28a78
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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