HCID 11120848, compound → HCID 14758908, compound

HRID 1700951Notes

Reaction equation

HRID 1700951 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C@H:12]([CH3:22])[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])C1C=CC=CC=1>C(O)C.C1CCCCC=1.[OH-].[OH-].[Pd+2]>[Si:15]([O:14][CH2:13][C@@H:12]([CH3:22])[CH2:11][CH2:10][CH2:9][OH:8])([C:18]([CH3:20])([CH3:21])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 1

HCID 11120848HCID 11120848, compound

Product 1

HCID 14758908HCID 14758908, compoundYield 162.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

Catalytic Transfer Hydrogenolysis Protocol: 48.5 mg of Pd(OH)2 on activated charcoal (20%) (Pearlman's catalyst) is added to a solution of (S)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 5 (485 mg, 1.5 mmol) in 12.0 ml of absolute ethanol and 6.0 ml of cyclohexene. The mixture is heated under ref lux until the reaction is completed (tic monitoring). If starting material can still be detected after 8 h, some catalyst is added and refluxing is continued until the reaction is completed. After cooling to room temperature the catalyst is filtered off. The filtrate is concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 5:1) affords (S)-5-(tert-butyldimethylsilyloxy)4-methyl-pentan-1-ol 6 (565 mg, 97%) as a colourless oil.

Workup

  1. temperatureThe mixture is heated under ref lux until the reaction
  2. additionsome catalyst is added
  3. temperaturerefluxing
  4. filtrationis filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customPurification of the residue by flash column chromatography (pentane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-8782e423e51d466c9810ec7b0db0211b
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

Loading…