Acetic Acid → HCID 53909061, compound

HRID 37627Notes

Reaction equation

HRID 37627 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])[CH3:3].[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][C@H:17]2[OH:21])[CH:8]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 152897542-[3,5-Bis(1,1-dimethylethyl)phenylmethyl]-cyclopentanone

Product 1

HCID 53909061HCID 53909061, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 710 mg (2.48 mmoles) of the title product of Example 5 in 25 ml of ethanol was added dropwise a solution of 188 mg (4.97 mmoles) of sodium borohydride in 3 ml of water. After 30 minutes, acetic acid was added, most of the ethanol was evaporated, the residue was partitioned between diethyl ether and dilute aqueous hydrochloric acid, the aqueous layer was further extracted with ether, and the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue using 15% ethyl acetate/hexane as eluent gave the title cis isomer (105 mg) and the title trans isomer (155 mg) as colorless oils. The structures were supported by 1H NMR.

Workup

  1. customwas evaporated
  2. customthe residue was partitioned between diethyl ether and dilute aqueous hydrochloric acid
  3. extractionthe aqueous layer was further extracted with ether
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customgave the title

Sources & evidence

ORD record
ord-fc1406fd61e340f0995cdc39f3b7c1b2
Source dataset
uspto-grants-1995_05
Patent number
US05420343

Reaction notes

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