Water → HCID 59401291, compound

HRID 2060851Notes

Reaction equation

HRID 2060851 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[CH2:13][NH2:14].[CH3:15][CH:16]([CH3:20])[CH2:17][CH:18]=O.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[CH2:13][NH:14][CH2:18][CH2:17][CH:16]([CH3:20])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 115523-MethylbutanalHCID 4311764Sodium borohydrideHCID 59401298HCID 59401298, compound

Product 1

HCID 59401291HCID 59401291, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-methoxynaphthalen-1-ylmethylamine (Preparation 12) (389 mg, 2.08 mmol) in MeOH (15 mL), was added 3-methylbutyraldehyde (223 μL, 2.08 mmol). The mixture was stirred for 16 h at rt under nitrogen before adding NaBH4 (236 mg, 6.24 mmol). After stirring for 1 h water (0.5 mL) was added and the solvent removed in vacuo. The mixture was partitioned between EtOAc (100 mL) and NaHCO3 (25 mL), the organic phase was washed with water (25 mL), brine (25 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (DCM: MeOH: NH4OH, 97:3:0.3 to 95:5:0.5) to give the title compound: RT=2.46 min; m/z (ES+)=258.1 [M+H]+.

Workup

  1. additionwas added
  2. customthe solvent removed in vacuo
  3. customThe mixture was partitioned between EtOAc (100 mL) and NaHCO3 (25 mL)
  4. washthe organic phase was washed with water (25 mL), brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo
  7. customthe residue purified by column chromatography (DCM: MeOH: NH4OH, 97:3:0.3 to 95:5:0.5)

Sources & evidence

ORD record
ord-13ed71ae6ef1418783972370872a5303
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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