tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 59025418, compound

HRID 2421065Notes

Reaction equation

HRID 2421065 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]3[NH:10][C:9]2=[O:17])[CH2:4][CH2:3]1.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>[O:17]=[C:9]1[N:8]([CH:5]2[CH2:4][CH2:3][N:2]([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)[CH2:7][CH2:6]2)[C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]2[NH:10]1

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate2×HCID 5003444Sodium cyanoborohydride2×HCID 131728947HCID 131728947, compound

Product 1

HCID 59025418HCID 59025418, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis-(+/−)-1-piperidin-4-yloctahydro-2H-benzimidazol-2-one Hydrochloride salt (263 mg, 1.01 mmol) in MeOH (5 mL) was added tert-butyl 4-oxopiperidine-1-carboxylate (241 mg, 1.21 mmol). The mixture was stirred at room temperature for 30 min before sodium cyanoborohydride (95 mg, 1.52 mmol) was added. The mixture was stirred overnight at room temperature, additional amount of tert-butyl 4-oxopiperidine-1-carboxylate and sodium cyanoborohydride (1 eq each) were added and stirred at room temperature for 3 more days. MeOH was concentrated in vacuo, the residue dissolved in dichloromethane (20 mL) and washed with water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. To provide the title compound (244 mg, 59%) MS (M+1): 407.4

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 3 more days
  3. concentrationMeOH was concentrated in vacuo
  4. dissolutionthe residue dissolved in dichloromethane (20 mL)
  5. washwashed with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d48ef55e6f5143fc9dfbd30661819577
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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