Sodium borohydride → (+/-)7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-ol

HRID 2120692Notes

Reaction equation

HRID 2120692 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:32])[CH:20]=[CH:21][C:22]3[CH:31]=[N:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:32])[CH:20]=[CH:21][C:22]3[CH:31]=[N:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 696661987-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-one

Product 1

HCID 69665953(+/-)7-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-1-quinoxalin-2-yl-hept-1-en-3-olYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the enone 22-2 (1.0 g, 2.2 mmol) in MeOH (50 mL) at 0° C. was treated with NaBH4 (0.092 g, 2.4 mmol). The ice bath was removed and the solution was stirred at room temperature for 1 hr. The reaction was quenched with water (25 mL) and extracted with EtOAc (3×125 mL). The organics were combined, dried (Na2SO4), concentrated in vacuo, and purified on silica gel (90:5:5 CHCl3:EtOAc:MeOH) to afford 0.26 g of 22-3.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with water (25 mL)
  3. extractionextracted with EtOAc (3×125 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified on silica gel (90:5:5 CHCl3:EtOAc:MeOH)

Sources & evidence

ORD record
ord-e17a913843da4086869a6ecb8fd2f21b
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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