Sodium borohydride → HCID 18630237, compound

HRID 725460Notes

Reaction equation

HRID 725460 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4](=[O:18])[C:5]1[C:10]([CH:11]=[O:12])=[CH:9][CH:8]=[C:7]([F:13])[C:6]=1[Si:14]([CH3:17])([CH3:16])[CH3:15])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4](=[O:18])[C:5]1[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[C:7]([F:13])[C:6]=1[Si:14]([CH3:16])([CH3:15])[CH3:17])[CH3:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14901674HCID 14901674, compound

Product 1

HCID 18630237HCID 18630237, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 41 (1.2 g, 4.1 mmol) and sodium borohydride (200 mg, 5.3 mmol) in ethanol (20 mL) were stirred at ambient temperature for 2 h. The solution was concentrated and partitioned between ether and 10% citric acid. The ether layer was washed with water and then brine, dried (MgSO4), concentrated, and recrystallized from cold hexanes to afford 1.0 g of the title compound, an 82% yield. m.p. 107°-108° C.

Workup

  1. concentrationThe solution was concentrated
  2. custompartitioned between ether and 10% citric acid
  3. washThe ether layer was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. concentrationconcentrated
  6. customrecrystallized from cold hexanes

Sources & evidence

ORD record
ord-9af566a6cfc74bae8a694c867fbc05e3
Source dataset
uspto-grants-1998_01
Patent number
US05705513

Reaction notes

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