3-(Piperidine-1-sulfonyl)benzoic acid → (3-(Piperidin-1-ylsulfonyl)phenyl)methanol

HRID 1919856Notes

Reaction equation

HRID 1919856 reaction equation
[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13](O)=[O:14])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1>[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([CH2:13][OH:14])[CH:16]=[CH:17][CH:18]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 7678893-(Piperidine-1-sulfonyl)benzoic acid

Product 1

HCID 65750537(3-(Piperidin-1-ylsulfonyl)phenyl)methanolYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (538 mg, 2.00 mmol) in dry THF (8 mL) under nitrogen was added a solution of borane-THF complex in dry THF (1.0 M, 8 mL, 8.00 mmol) and the mixture then stirred for 18 hours at room temperature. The reaction was then quenched by the addition of excess methanol and evaporated in vacuo. The residue was partitioned between ethyl acetate and 2N HCl, and the separated organic layer washed successively with water and saturated brine, before being dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified using automated flash column chromatography on silica gel (gradient of 0 to 60% ethyl acetate in petrol) to afford (3-(piperidin-1-ylsulfonyl)phenyl)methanol (320 mg, 1.25 mmol, 63%).

Workup

  1. customThe reaction was then quenched by the addition of excess methanol
  2. customevaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 2N HCl
  4. washthe separated organic layer washed successively with water and saturated brine
  5. dry with materialbefore being dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-5e71e2327d6b4abe8e41cfd13c0cf3ac
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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