tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 59025456, compound

HRID 2421081Notes

Reaction equation

HRID 2421081 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:8][C:9]#[N:10].[Na].O=[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:9]([CH2:8][C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[NH:1][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)#[N:10]

Participants

7

Reactant 4

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 55288821HCID 55288821, compound

Product 1

HCID 59025456HCID 59025456, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

[(1R,2S)-2-aminocyclohexyl]acetonitrile (1.1 g) was dissolved in MeOH (10 mL) and sodium methoxyde (0.45 mL) was added. The mixture was stirred for 15 minutes then tert-butyl 4-oxopiperidine-1-carboxylate (0.85 g, 4.27 mmol) was added. A solution containing sodium cyanoborohydride (0.36 g, 5.22 mmol) and zinc chloride (0.35 g, 2.60 mmol) in MeOH (2 mL) was then added drop wise and the mixture stirred at room temperature. The solvent was then removed under reduced pressure and the residue was diluted in dichloromethane and was washed with 1N NaOH and brine. The crude was purified by high pH prep LCMS to provide 0.6 g of the title compound. MS (M+1): 322.27

Workup

  1. additionwas then added drop wise
  2. stirringthe mixture stirred at room temperature
  3. customThe solvent was then removed under reduced pressure
  4. additionthe residue was diluted in dichloromethane
  5. washwas washed with 1N NaOH and brine
  6. customThe crude was purified by high pH

Sources & evidence

ORD record
ord-439986fa559945dea2325a101c6c6b0e
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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