Sodium borohydride → 1-[8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanol

HRID 1530703Notes

Reaction equation

HRID 1530703 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[C:18](=[O:20])[CH3:19])[C:14]1[N:10]([CH:11]=[C:12]([C:21]3[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[C:23]([CH3:29])[N:22]=3)[N:13]=1)[CH2:9][CH2:8][O:7]2>CO>[F:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[CH:18]([OH:20])[CH3:19])[C:14]1[N:10]([CH:11]=[C:12]([C:21]3[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[C:23]([CH3:29])[N:22]=3)[N:13]=1)[CH2:9][CH2:8][O:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 683130591-{12-Fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-one

Product 1

HCID 683128551-[8-Fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-9-yl]ethanolYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred suspension of NaBH4 (638 mg, 16.8 mmol) in MeOH (15 mL), was added a solution of 1-{12-fluoro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethan-1-one (1.55 g, 4.20 mmol) in MeOH (15 mL) at 0° C. under a nitrogen atmosphere. After the addition was completed, the cooling bath was removed and the mixture was stirred at room temperature for 1 h. After removal of the solvent, the residue was purified by silica gel chromatography using 5% dichloromethane in methanol as eluant to give the title compound (1.5 g, 96% yield) as a white solid. LCMS m/z [M+H]+ 372.1

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. customAfter removal of the solvent
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-01f4631a61a84b73b091bae59eda5e63
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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