Sodium borohydride → HCID 68817151, compound

HRID 736840Notes

Reaction equation

HRID 736840 reaction equation
[CH3:1][C:2]([S:5]([N:7]=[C:8]1[CH2:16][CH2:15][CH2:14][C:9]21[O:13][CH2:12][CH2:11][CH2:10]2)=[O:6])([CH3:4])[CH3:3].[BH4-].[Na+]>C1COCC1.CO>[CH3:4][C:2]([S:5]([NH:7][CH:8]1[CH2:16][CH2:15][CH2:14][C:9]21[O:13][CH2:12][CH2:11][CH2:10]2)=[O:6])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68817114HCID 68817114, compound

Product 1

HCID 68817151HCID 68817151, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound prepared in Example 1 above (1.73 g, 7.10 mmol) in THF (50 mL) was treated with a solution of sodium borohydride (462 mg, 12.2 mmol) in methanol (10 mL). After stirring for 45 min at room temperature, the reaction was quenched by the addition of saturated ammonium chloride (10 mL) and the resulting mixture was extracted with ethyl acetate. The reaction mixture was then concentration, and the residue was purified by flash chromatography to yield the title compound as a colorless oil.

Workup

  1. customthe reaction was quenched by the addition of saturated ammonium chloride (10 mL)
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. concentrationconcentration
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c1aac1afa6a149e99802ba677c8eb440
Source dataset
uspto-grants-2009_09
Patent number
US07595409B2

Reaction notes

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