Potassium Carbonate → HCID 67506401, compound

HRID 473823Notes

Reaction equation

HRID 473823 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O.C(OCC)(=O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C@H:7]2[CH2:6][C@H:5]([OH:4])[CH2:10][CH2:9][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68756521HCID 68756521, compound

Product 1

HCID 67506401HCID 67506401, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A suspention of (±)-(2R,4R)-tert-butyl 4-acetoxy-2-(4-fluorophenyl)piperidine-1-carboxylate (150 mg, 0.40 mmol) and potassium carbonate (1.0 g) in methanol:water 10:1 (11 mL) was stirred for 1 hour then diluted with ethyl acetate (40 mL) and washed with water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give (±)-(2R,4R)-tert-butyl 2-(4-fluorophenyl)-4-hydroxypiperidine-1-carboxylate (117 mg, 99% yield). 1H NMR (400 MHz, d6-DMSO): 7.17 (m, 4H), 5.34 (br d, 1H), 4.73 (d, 1H), 4.34 (br d, 1H), 3.41 (m, 1H), 2.67 (m, 1H), 2.42 (br d, 1H), 1.57 (m, 1H), 1.38 (s, 9H).

Workup

  1. washwashed with water (25 mL) and brine (25 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75c7ec9095a84081b3358240620d6547
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

Loading…