Ethanol → HCID 86606465, compound

HRID 749629Notes

Reaction equation

HRID 749629 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:12](=CC=O)[CH:11]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:36][CH2:37][OH:38]>>[CH2:1]([O:8][CH:9]1[CH2:14][CH:13]([O:15][Si:16]([C:19]([CH3:21])([CH3:22])[CH3:20])([CH3:18])[CH3:17])[C:12](=[C:37]([OH:38])[CH3:36])[CH:11]([O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:28])[CH3:29])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 72388329HCID 72388329, compound

Product 1

HCID 86606465HCID 86606465, compoundYield 98%

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 31 (288 mg, 0.587 mmol, 31a:31b=ca. 1:2) in EtOH (1 mL) cooled to 0° C. was added NaBH4 (26.6 mg, 0.704 mmol). After, the reaction mixture was stirred for 1 h at 0° C., into the reaction mixture was poured ice water, and extracted with AcOEt. The organic layer was washed with saturated brine, and dried over anhydrous MgSO4. Solvents were removed in vacuo, and the residue was purified by silica gel column chromatography (10 g; 15% AcOEt/hexane) to yield Compound 32 (283.3 mg, 98%) as a mixture of two stereoisomers. The ratio of the stereoisomers constituting the mixture was ca. 2:1. It was impossible to know whether the major product was aS*,2R,6R isomer or aR*,2R,6R isomer.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous MgSO4
  4. customSolvents were removed in vacuo
  5. customthe residue was purified by silica gel column chromatography (10 g; 15% AcOEt/hexane)

Sources & evidence

ORD record
ord-3524457db5034284bf10df97496138e3
Source dataset
uspto-grants-2008_07
Patent number
US07402688B2

Reaction notes

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