Borane;tetrahydrofuran → tert-Butyl 3-[(2-fluoroanilino)methyl]piperidine-1-carboxylate

HRID 988793Notes

Reaction equation

HRID 988793 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=O)[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:9]1)=[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][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 51254627HCID 51254627, compound

Product 1

HCID 54188486tert-Butyl 3-[(2-fluoroanilino)methyl]piperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-fluorophenylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester (2) (1.13 g, 3.5 mmol) in THF (4 ml) at 0° C. was added BH3-THF solution (1.0 M, 3.5 ml) slowly. The mixture was refluxed for 2 hrs. The reaction was quenched by slow addition of MeOH at 0° C. The solvent was removed by evaporation. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 85:15) to give 3-[(2-Fluorophenylamino)methyl]piperidin-1-carboxylic acid tert-butyl ester (3) as a colorless oil (0.97 g, 90%).

Workup

  1. temperatureThe mixture was refluxed for 2 hrs
  2. customThe reaction was quenched by slow addition of MeOH at 0° C
  3. customThe solvent was removed by evaporation
  4. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 85:15)

Sources & evidence

ORD record
ord-59c0e9e0c8bb4ae09f8dabbea9f8e555
Source dataset
uspto-grants-2003_10
Patent number
US06635661B2

Reaction notes

Loading…