Acetic Acid → HCID 57678157, compound

HRID 419354Notes

Reaction equation

HRID 419354 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH:18]2[CH2:19][CH2:20][N:15]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:16][CH2:17]2)[CH2:4][CH2:3]1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 693814-MethylpiperidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57678157HCID 57678157, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution, 1 h, at 0° C. of 4-methylpiperidine (15.0 g, 151 mmol), 1-boc-4-piperidone (30.1 g, 151 mmol) and HOAc (18.2 g, 303 mmol) in THF (100 mL) was added sodium triacetoxyborohydride (64.2 g, 303 mmol) in 3 portions. The mixture was stirred at rt for 18 h. The reaction was neutralized with saturated K2CO3 and the pH was adjusted to 8 with saturated Na2CO3. The mixture was diluted with DCM and separated. The organic layer was washed with H2O and concentrated to provide the title compound of step A (33.0 g, 117 mmol, 77%). 1H NMR (400 MHz, CDCl3) δ ppm 0.71-0.90 (m, 3H), 1.11-1.20 (m, 2H), 1.31-1.50 (m, 9H), 1.50-1.65 (m, 1H), 1.70-1.90 (m, 4H), 2.01-2.30 (m, 2H), 2.71-3.10 (m, 4H), 3.60-3.91 (m, 5H).

Workup

  1. customseparated
  2. washThe organic layer was washed with H2O
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dd88b5acebf846d18418c21e5750aa2d
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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