Water → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1269791Notes

Reaction equation

HRID 1269791 reaction equation
B.O1CCCC1.[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](O)=[O:21])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])O.[Na+].O>O1CCCC1>[OH:21][CH2:20][CH:17]1[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M-borane/tetrahydrofuran solution (4.36 ml, 4.36 mmol) was added dropwise to a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1.0 g, 4.36 mmol) in tetrahydrofuran (20 ml) at 0° C. After 1 hour, the mixture thus obtained was warmed up to room temperature. After another 6 hours, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture and the resulting mixture was poured into water (100 ml) and extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (715 mg, 76%).

Workup

  1. customthe mixture thus obtained
  2. waitAfter another 6 hours
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customThe organic layer dried
  6. concentrationwas concentrated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-748bb6fd344940dd9b3e7bf06afcaa52
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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