Sodium borohydride → HCID 59381640, compound

HRID 2354546Notes

Reaction equation

HRID 2354546 reaction equation
[CH2:1]1[C:6]2[C:7]3[C:18](=[O:19])[N:11]4[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]4=[N:9][C:8]=3[S:20][C:5]=2[C:4](=[O:21])[CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1.CCO>[OH:21][CH:4]1[C:5]2[S:20][C:8]3[N:9]=[C:10]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]4[C:18](=[O:19])[C:7]=3[C:6]=2[CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11381102HCID 11381102, compound

Product 1

HCID 59381640HCID 59381640, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To compound 3d (200 mg, 0.66 mmol) in 5 ml of THF and 15 ml of EtOH, NaBH4 (33 mg, 0.86 mmol) was added and the reaction mixture was stirred for 15 minutes. The reaction was quenched with water and extracted with CH2Cl2. The organic layer was washed with brine and dried with NaaSO2. After filtration the solvent was evaporated. The product was purified by flash chromatography using CH2Cl2/EtOAc 1:1 as an eluent.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. customdried with NaaSO2
  5. filtrationAfter filtration the solvent
  6. customwas evaporated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-0681626ef0fa4cbea5572f13d2ccf37a
Source dataset
uspto-grants-2010_07
Patent number
US07754709B2

Reaction notes

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