Cyclohexanone → HCID 59750684, compound

HRID 422246Notes

Reaction equation

HRID 422246 reaction equation
[BH3-]C#N.[Na+].[NH2:5][CH2:6][CH:7]1[CH2:16][CH2:15][CH2:14][C:13]2[C:12]([O:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)=[CH:11][CH:10]=[CH:9][C:8]1=2.[C:27]1(=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>CC(O)=O.CO>[CH:27]1([NH:5][CH2:6][CH:7]2[CH2:16][CH2:15][CH2:14][C:13]3[C:12]([O:17][C:18]4[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=4)=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 59750691HCID 59750691, compound2×

Product 1

HCID 59750684HCID 59750684, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

Add NaBH3CN (63 mg, 1.00 mmol) to a solution of 6-(5-aminomethyl-5,6,7,8-tetrahydro naphthalen-1-yloxy)-nicotinamide (intermediate 20, 148 mg, 0.500 mmol) and cyclohexanone (98 mg, 1.00 mmol) dissolved in 5% AcOH/MeOH (5 ml) and stir at ambient temperature for 16 hours. Concentrate the reaction mixture and redissolved in EtOAc. Wash the EtOAc solution with 5% aq. KOH and brine before drying (MgSO4) and concentrating. Purify on silica gel (5% (1N NH3/MeOH)/DCM) to obtain 145 mg of the title compound as a white foam. Mass spectrum (ion spray): m/z=380 (M+1); 1HNMR (CDCl3): 8.56 (s, 1H), 8.15 (d, 1H), 7.22-7.14 (m, 2H), 6.90 (m, 2H), 5.79 (br. s, 2H), 2.99 (m, 1H), 2.96-2.79 (m, 2H), 2.63-2.41 (m, 3H), 1.91 (m, 2H), 1.85-1.67 (m, 6H), 1.31-1.04 (m, 6H).

Workup

  1. concentrationConcentrate the reaction mixture
  2. dissolutionredissolved in EtOAc
  3. washWash the EtOAc solution with 5% aq. KOH and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating
  6. customPurify on silica gel (5% (1N NH3/MeOH)/DCM)

Sources & evidence

ORD record
ord-13ebf9b4050b4f3fba4e2a24fd490426
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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