HCID 57274845, compound → HCID 86584299, compound

HRID 479315Notes

Reaction equation

HRID 479315 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][C@@H:10]1[OH:29])[CH3:8])[CH3:3]>C(OCC)(=O)C.[Pd]>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][C@@H:18]([OH:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][C@@H:10]1[OH:29])[CH3:8])[CH3:1]

Participants

4

Reactant 1

HCID 57274845HCID 57274845, compound

Product 1

HCID 86584299HCID 86584299, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Cholest-5-ene-3β,16β-diol (600 mg, 1.4 mmol) in ethyl acetate (15 mL) was hydrogenated at atmospheric pressure over 5% palladium on carbon for 3 days. Removal of catalyst by filtration through Celite and purification of the residue by flash chromatography gave the title compound (190 mg). The 1H-NMR spectrum (CDCl3, d) showed characteristic signals at: 0.81 (s, 3H), 0.86 (s, 3H), 0.89 (s, 3H), 3.55 (m, 1H, H-3), 4.31 (m, 1H, H-16). The 13C-NMR spectrum (CDCl3, d) showed characteristic signals at: 71.7 (C-3), 72.9 (C-8). The mass spectrum showed characteristic peaks at: 404.4 (M+).

Workup

  1. customRemoval of catalyst
  2. filtrationby filtration
  3. customthrough Celite and purification of the residue by flash chromatography

Sources & evidence

ORD record
ord-632fe8e877f44c24a66ebcd8eb4ab1d0
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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