Ethyl 4-oxo-1-piperidinecarboxylate → HCID 24883240, compound

HRID 2421084Notes

Reaction equation

HRID 2421084 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:15]3[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)[CH2:9][C:8]2=[O:16])[CH2:3][CH2:2]1.C[O-].[Na+].O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[O:16]=[C:8]1[CH2:9][C@@H:10]2[C@H:15]([CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]1[CH:4]1[CH2:3][CH2:2][N:1]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 5003444Sodium cyanoborohydrideHCID 10942334Sodium MethoxideHCID 67214968HCID 67214968, compound

Product 1

HCID 24883240HCID 24883240, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

The crude of (3aR)-1-piperidin-4-yloctahydro-2H-indol-2-one (110 mg) was dissolved in MeOH (3 mL) and sodium methoxide (25 μL) was added followed by ethyl 4-oxopiperidine-1-carboxylate (77 μL, 0.5 mmol. A solution of sodium cyanoborohydride (35 mg, 0.5 mmol) and zinc chloride (29 mg, 0.25 mmol) in MeOH (1 mL) was added drop wise at room temperature and the mixture was stirred at room temperature over night. The solvent was then removed under reduced pressure and the residue dissolved in dichloromethane (60 mL). Washed with 1N NaOH (5 mL) and brine, dried and concentrated in vacuo. The residue was purified by high pH Prep LCMS to provide the title compound. 1H NMR (400 MHz, METHANOL-D4): δ ppm 1.24 (t, J=6.45 Hz, 3H), 1.27-1.49 (m, 6H), 1.62 (d, J=12.50 Hz, 2H), 1.55-1.73 (m, 1H), 1.78 (d, J=9.77 Hz, 1H), 1.82-2.17 (m, 7H), 2.18-2.33 (m, 3H), 2.33-2.43 (m, 1H), 2.49 (t, J=12.11 Hz, 1H), 2.69-2.86 (m, 2H), 3.02 (t, J=10.94 Hz, 2H), 3.12 (t, J=10.16 Hz, 1H), 3.72-3.85 (m, 1H), 4.09 (q, J=7.03 Hz, 2H), 4.16 (d, J=12.89 Hz, 2H). MS (M+1): 378.3

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane (60 mL)
  3. washWashed with 1N NaOH (5 mL) and brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by high pH Prep LCMS

Sources & evidence

ORD record
ord-29db87eb3c4c4719821c0e3850d6dca7
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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