Sodium borohydride → HCID 178450838, compound

HRID 1518389Notes

Reaction equation

HRID 1518389 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][C:5]1[C:6]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:7][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[C:14]([C:21](=[O:40])/[N:22]=[C:23]4\[S:24][C:25]5[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=5[N:27]\4[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[CH:9][CH:10]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[N:7][C:8]([N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[C:14]([C:21](=[O:40])/[N:22]=[C:23]4\[S:24][C:25]5[CH:39]=[CH:38][CH:37]=[CH:36][C:26]=5[N:27]\4[CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178450837HCID 178450837, compound

Product 1

HCID 178450838HCID 178450838, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 94E (0.91 g, 1.351 mmol) in THF (30 mL) and methanol (5 mL) was treated with NaBH4 (0.102 g, 2.7 mmol). The reaction mixture was heated under reflux for 1 hour. The solvents were removed under vacuum. The residue was re-dissolved in EtOAc and treated with water. The organic layer was separated, and the aqueous layer was extracted with additional EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography to give 0.75 g of the title compound 94F (82%): APCI (+)LC/MS: 675 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvents were removed under vacuum
  4. dissolutionThe residue was re-dissolved in EtOAc
  5. additiontreated with water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with additional EtOAc
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a04391b07f15421188990d0f72b097c9
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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