Water → (1-(Methylsulfonyl)piperidin-4-yl)methanol

HRID 429819Notes

Reaction equation

HRID 429819 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]1)=O)C.O>O1CCCC1>[CH3:21][S:18]([N:15]1[CH2:16][CH2:17][CH:12]([CH2:10][OH:9])[CH2:13][CH2:14]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 669104Ethyl 1-(methylsulfonyl)piperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18352755(1-(Methylsulfonyl)piperidin-4-yl)methanolYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

A solution of 1.0 M lithium aluminum hydride (200 ml, 0.2 mole) in tetrahydrofuran was added dropwise to a solution of 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 0.29 mole) in tetrahydrofuran (500 ml) at about +5° C. The reaction mixture was stirred at 5-10° C. for 15 minutes. Water (10 ml) was added dropwise and the mixture was filtered. The filtrate was concentrated under reduced pressure and triturated with 50% ethyl ether-hexane (100 ml). The resulting white solid was collected and dried to give 1-methanesulfonylpiperidine-4-methanol (46 grams, 82%), m.p. 96-97° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customtriturated with 50% ethyl ether-hexane (100 ml)
  4. customThe resulting white solid was collected
  5. customdried

Sources & evidence

ORD record
ord-cc3d3a4026a64e65a09748f3365d0819
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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