Water → (1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol

HRID 1913165Notes

Reaction equation

HRID 1913165 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22](OC)=[O:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[BH4-].[Na+].O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]2)(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 58494546Methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate

Product 1

HCID 58494552(1-{[4-(Pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidine-4-carboxylate (0.40 g, 1.11 mmol) in anhydrous methanol (8 mL) is added sodium borohydride (0.59 g, 15.5 mmol). After 18 h water (20 mL) is added. The resulting solid is filtered, washed with water and suspended in MeCN. The suspension is concentrated under reduced pressure to give 0.26 g (72%) of 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol. m/z=333 [M++H].

Workup

  1. filtrationThe resulting solid is filtered
  2. washwashed with water
  3. concentrationThe suspension is concentrated under reduced pressure
  4. customto give 0.26 g (72%) of 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}piperidin-4-yl)methanol

Sources & evidence

ORD record
ord-c45bff9584af4854942b7254b7da956a
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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