3-Methylbutanal → HCID 11199441, compound

HRID 422243Notes

Reaction equation

HRID 422243 reaction equation
[CH:1](=O)[CH2:2][CH:3]([CH3:5])[CH3:4].[NH2:7][CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)[CH:12]=[CH:11][C:10]1=2.[BH4-].[Na+]>CO>[CH3:4][CH:3]([CH3:5])[CH2:2][CH2:1][NH:7][CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 59750673HCID 59750673, compound2×

Product 1

HCID 11199441HCID 11199441, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add isovaleraldehyde (64.5 mg, 0.750 mmol) to a solution of 6-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (intermediate 21, 148 mg, 0.500 mmol) dissolved in MeOH (5 mL) and stir at ambient temperature for 1.5 hours before adding NaBH4 (38 mg, 1.00 mmol). After stirring for an additional two 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 123 mg of the title compound as a white foam. Mass spectrum (ion spray): m/z=368 (M+1); 1HNMR (CDCl3): 8.59 (s, 1H), 8.15 (d, 1H), 7.25 (d, 1H), 6.94 (d, 1H), 6.89 (d, 1H), 6.85 (s, 1H), 5.82 (br. s, 2H), 2.97 (m, 1H), 2.84 (m, 2H), 2.76 (m, 2H), 2.66 (m, 2H), 1.85 (m, 3H), 1.74 (m 1H), 1.62 (m, 1H), 1.41 (m, 2H), 0.90 (d, 6H).

Workup

  1. stirringAfter stirring for an additional two hours
  2. concentrationconcentrate the reaction mixture
  3. dissolutionredissolved in EtOAc
  4. washWash the EtOAc solution with 5% aq. KOH and brine
  5. dry with materialbefore drying (MgSO4)
  6. concentrationconcentrating
  7. customPurify on silica gel (5% (1N NH3/MeOH)/DCM)

Sources & evidence

ORD record
ord-5dbcd585efe4462b9f3d5257236298c4
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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