1-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acid → N-Boc-piperidine-2-methanol

HRID 460201Notes

Reaction equation

HRID 460201 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 2763853N-Boc-piperidine-2-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (50 g, 218.1 mmol) in dry THF (300 mL) was cooled to −78° C. followed by adding BH3-THF solution (261.7 mL, 260.0 mmol) dropwise over 1 h. The resulting mixture was warmed to RT and stirred for 48 h. The reaction was quenched with HOAc/H2O (1:1 ratio, 100 mL). The resulting mixture was partitioned between EtOAc and sat. NaHCO3. The organic layer was washed with more sat. NaHCO3, H2O, brine, and dried over MgSO4. Concentration in vacuo gave a white solid. MS m/z: 216.2 (M+H). Calc'd. for C11H21NO3-215.15.

Workup

  1. customThe reaction was quenched with HOAc/H2O (1:1 ratio, 100 mL)
  2. customThe resulting mixture was partitioned between EtOAc and sat. NaHCO3
  3. washThe organic layer was washed with more sat. NaHCO3, H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationConcentration in vacuo
  6. customgave a white solid

Sources & evidence

ORD record
ord-6996af5368c74525bd2ed8a6a1497bc7
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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