4-(4-Fluorobenzoyl)piperidine → HCID 68809285, compound

HRID 434293Notes

Reaction equation

HRID 434293 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][N:31]1[CH2:32][CH2:33][CH:28]([C:26](=[O:27])[C:23]2[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=2)[CH2:29][CH2:30]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 7020444tert-butyl N-[(2R)-1-oxo-3-phenylpropan-2-yl]carbamate

Product 1

HCID 68809285HCID 68809285, compound

Procedure

A solution of ((R)-1-benzyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (0.5 g, 2.0 mmol), (4-fluoro-phenyl)-piperidin-4-yl-methanone (0.414 g, 2.0 mmol) and sodium triacetoxyborohydride (0.638 g, 3.0 mmol) in tetrahydroftiran (20 ml) is stirred at ambient temperature for 24 hours. The solvent is evaporated and the residue redissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The dichloromethane is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (ethylacetate:hexane, 3:1 elution) to afford {(R)-1-benzyl-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}carbamic acid tert-butyl ester. [MH]+441.3.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue redissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe dichloromethane is dried over magnesium sulphate
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (ethylacetate:hexane, 3:1 elution)

Sources & evidence

ORD record
ord-a210c31d5c19429ab6f1391b0b252db9
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

Loading…