Sodium borohydride → HCID 59441906, compound

HRID 1014351Notes

Reaction equation

HRID 1014351 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH3:21])[CH:12]=2)[CH2:6][CH2:5]1)[CH3:3].[BH4-].[Na+]>C1COCC1.CO>[CH3:3][CH:2]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH3:21])[CH:12]=2)[CH2:6][CH2:5]1)[CH3:1]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59441891HCID 59441891, compound

Product 1

HCID 59441906HCID 59441906, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(1-methylethyl)-4-[3-(methyloxy)-4-nitrophenyl]hexahydro-1H-1,4-diazepine (0.565 g, 1.92 mmol) was suspended in 5 mL THF and 10 mL MeOH. NiCl2-6H2O (138 mg, 0.576 mmol) was added followed by slow addition of NaBH4 (218 mg, 5.76 mmol). The reaction mixture was adsorbed on SiO2 and purified via column chromatography to afford 4-[4-(1-methylethyl)hexahydro-1H-1,4-diazepin-1-yl]-2-(methyloxy)aniline (364 mg, 1.38 mmol). 1H NMR (400 MHz, DMSO-d6)δ ppm 0.89-1.06 (m, 6 H) 1.71-1.88 (m, 2 H) 2.69 (br. s., 2 H) 2.81-2.97 (m, 1 H) 3.23-3.47 (m, 6H) 3.66-3.77 (m, 3 H) 3.82-4.27 (m, 2 H) 6.08 (br. s., 1 H) 6.25 (br. s., 1 H) 6.49 (br. s., 1 H). ESIMS (M+H)+=264.

Workup

  1. custompurified via column chromatography

Sources & evidence

ORD record
ord-0a8293c86c7e40dd945546b49be17fb7
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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