tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 59025402, compound

HRID 2421069Notes

Reaction equation

HRID 2421069 reaction equation
[CH3:1][N:2]1[C@H:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:5]2[N:4]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:3]1=[O:17].O=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH3:1][N:2]1[C@H:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:5]2[N:4]([CH:11]2[CH2:16][CH2:15][N:14]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:13][CH2:12]2)[C:3]1=[O:17]

Participants

6

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 59025432HCID 59025432, compound

Product 1

HCID 59025402HCID 59025402, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

(3aS,7aS)-1-methyl-3-piperidin-4-yloctahydro-2H-benzimidazol-2-one (1.13 g, 4.75 mmol) was dissolved in MeOH (10 mL) and tert-butyl 4-oxopiperidine-1-carboxylate (1 g, 5.02 mmol) was then added. A solution containing sodium cyanoborohydride (0.49 g, 7.10 mmol) and ZnCl2 (0.38 g, 2.79 mmol) in MeOH (2 mL) was added and the mixture and stirred at room temperature overnight. The solvent was then removed under reduced pressure and the residue was dissolved in dichloromethane (150 mL). Organic layer was washed with 1N NaOH (10 mL) and brine (5 mL), dried and concentrated in vacuo. The residue was purified by column chromatography (dichloromethane-MeOH gradient) to provide the title compound as a white solid (1.6 g, 80%). MS (M+1): 421.4.

Workup

  1. additionwas added
  2. customThe solvent was then removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (150 mL)
  4. washOrganic layer was washed with 1N NaOH (10 mL) and brine (5 mL)
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (dichloromethane-MeOH gradient)

Sources & evidence

ORD record
ord-fa56bfc732dd47ee946713608323d183
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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