Sodium borohydride → HCID 11080708, compound

HRID 398003Notes

Reaction equation

HRID 398003 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:3]=1[CH:4]=[O:5].[BH4-].[Na+]>CO.C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([C:24]([CH3:25])([CH3:26])[CH3:27])([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23001298HCID 23001298, compound

Product 1

HCID 11080708HCID 11080708, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 1, Step A (8.87 g, 20.2 mmol) was dissolved in methanol (50 mL) and methylene chloride (20 mL). Sodium borohydride (764 mg, 20.2 mmol) was added in portions at 0° C., and the solution was stirred for 2 hours. The reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution ceased. The resulting suspension was concentrated in vacuo and then partitioned between methylene chloride (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide the title product as a yellow oil which was sufficiently pure for use in the next step.

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution
  2. concentrationThe resulting suspension was concentrated in vacuo
  3. custompartitioned between methylene chloride (50 mL) and saturated aqueous sodium bicarbonate (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with methylene chloride (3×100 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d025209c2ceb469c87a959de64c4e453
Source dataset
uspto-grants-2003_08
Patent number
US06610722B2

Reaction notes

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