Hydrochloric Acid → HCID 9800248, compound

HRID 1764970Notes

Reaction equation

HRID 1764970 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:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=[O:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].Cl>O1CCCC1>[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:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([OH:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[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:13]3[CH2:14][CH2:15][C:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@@H:18]([OH:28])[CH:17]=4)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3611392Lithium tri-s-butylborohydrideHCID 15871124HCID 15871124, compound

Product 2

HCID 9800248HCID 9800248, compoundHCID 9800249HCID 9800249, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 520 mg cholesta-4,8-dien-3-one in 45 ml tetrahydrofuran 1.70 ml of a L-Selectride solution (1 N, in tetrahydrofuran) are added dropwise at −75° C. The reaction mixture is warmed to room temperature within 4 hours, poured into hydrochloric acid (1 N) and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of hexane and ethyl acetate to give 286 mg cholesta-4,8-dien-3β-ol and 20 mg cholesta-4,8-dien-3α-ol as white solids.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customAfter evaporation of the solvent the residue
  7. customis chromatographed with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-cd4a606e533444f5aaa6ed0b9c6a8e4d
Source dataset
uspto-grants-2007_06
Patent number
USRE039678E1

Reaction notes

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