Lithium tri-s-butylborohydride → (1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanol

HRID 517380Notes

Reaction equation

HRID 517380 reaction equation
[CH2:1]([C@@H:4]1[C@@H:8](/[CH:9]=[CH:10]/[C@@H:11]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C@H:7]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:6][C:5]1=[O:40])[CH:2]=[CH2:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[CH2:1]([C@@H:4]1[C@@H:8](/[CH:9]=[CH:10]/[C@@H:11]([O:24][Si:25]([CH2:26][CH3:27])([CH2:30][CH3:31])[CH2:28][CH3:29])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C@H:7]([O:32][Si:33]([C:36]([CH3:38])([CH3:37])[CH3:39])([CH3:35])[CH3:34])[CH2:6][C@@H:5]1[OH:40])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 131733344(2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanone

Product 1

HCID 131733345(1 S,2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanolYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 ml three-necked flask was flame dried and allowed to be cooled under nitrogen. (2R,3R,4R)-2-allyl-4-(tert-butyldimethylsilyloxy)-3-((R,E)-3-(triethylsilyloxy)-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentanone (2.68 g, 4.48 mmol) and 30 ml tetrahydrofuran were added to the reaction flask, followed by dropwise addition of L-Selectride (4 ml, 1M in tetrahydrofuran) at −70° C. Then, the reaction mixture was warmed to room temperature and quenched by 30 ml saturated aqueous ammonium chloride. The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography and then concentrated under reduced pressure to provide 2.5 g of the title compound (93% yield).

Workup

  1. temperatureA 500 ml three-necked flask was flame
  2. customdried
  3. temperatureto be cooled under nitrogen
  4. customquenched by 30 ml saturated aqueous ammonium chloride
  5. customseparated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe solid was filtered off
  9. customorganic solvent was evaporated off under vacuum
  10. customThe crude product was purified by chromatography
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f78925028d144a4aa0144246c0e0160
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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