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

HRID 1068496Notes

Reaction equation

HRID 1068496 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([C:12](O)=[O:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CO>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([CH2:12][OH:13])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-t-butoxycarbonyl isonipecotic acid (15.0 g, 65.4 mmol) from example 3 step A, in anhydrous THF (50 ml), was added borane (65.4 ml of a 1M solution in THF, 65.4 mmol) at room temperature. After 72 hours methanol (50 ml) was added and the solvent evaporated in vacuo. The residue was dissolved in methanol (100 ml) and the solvent evaporated in vacuo. The eesidue was partitioned between EtOAc and NaHCO3, the organic layer separated and washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by chromatography (Silica gel, eluting with 50% EtOAc in hexanes ) to afford the title compound.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol (100 ml)
  3. customthe solvent evaporated in vacuo
  4. customThe eesidue was partitioned between EtOAc and NaHCO3
  5. customthe organic layer separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography (Silica gel, eluting with 50% EtOAc in hexanes )

Sources & evidence

ORD record
ord-bde7729186934bb08ac30917741efedb
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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