Sodium borohydride → HCID 24976464, compound

HRID 505360Notes

Reaction equation

HRID 505360 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH:6]=[N:7][CH2:8][CH:9]([O:12][CH3:13])[O:10][CH3:11].[BH4-].[Na+]>CO>[CH3:20][O:19][C:15]1[CH:14]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:16]=1[O:17][CH3:18])[CH2:6][NH:7][CH2:8][CH:9]([O:10][CH3:11])[O:12][CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 11460264HCID 11460264, compound

Product 1

HCID 24976464HCID 24976464, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Imine (11c, 14.47 g, 0.05112 mol) was dissolved methanol (100 mL) and NaBH4 (2 g×3) was added over 5 h while stirring the reaction mixture at room temperature. After 3 h the TLC indicated there still was starting material and more NaBH4 (2 g) was added. The reaction did not go to completion leaving 25% of the starting material unreacted. The reaction was quenched with methanol (200 mL) and the reaction mixture was concentrated and then diluted with chloroform (300 μL) and filtered to remove the precipitate. The filtrate was washed with water (4×200 mL), brine (200 mL), dried (Na2SO4), and concentrated. The mixture was dissolved in ethanol (100 mL) and NaBH4 (2.5 g) was added. The reaction was stirred at room temperature for 4 h and then it was heated for 12 h at 80° C. The reaction mixture was diluted with methanol (50 mL) and concentrated. It was then dissolved in chloroform (250 mL) and washed with water (2×300 mL), brine (250 mL), dried (Na2SO4), and concentrated to provide a yellow oil (14.57 g, 100%). 1H NMR (300 MHz CDCl3) 6.47 (s, 2H), 4.39 (t, J=5.4 Hz, 1H), 3.76 (s, 6H), 3.73 (s, 3H), 3.65 (s, 2H), 3.28 (s, 6H), 2.65 (d, J=5.4 Hz, 2H).

Workup

  1. additionwas added over 5 h

Sources & evidence

ORD record
ord-393052a6040b4293aa4875d5a15b4f57
Source dataset
uspto-grants-2010_08
Patent number
US07781445B2

Reaction notes

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