Aluminium lithium hydride → (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol

HRID 388732

Reaction equation

HRID 388732 reaction equation
C([O:7][CH2:8][C@H:9]([C@@H:11]1[C@:19]2([CH3:20])[C@H:14]([C@@H:15]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12]1)[CH3:10])(=O)C(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Si:22]([O:21][C@H:15]1[CH2:16][CH2:17][CH2:18][C@@:19]2([CH3:20])[C@H:14]1[CH2:13][CH2:12][C@@H:11]2[C@H:9]([CH3:10])[CH2:8][OH:7])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68939165HCID 68939165, compound

Product 1

HCID 15230899(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-30 °C

Procedure

The compound of Example 10D (6.45 g, 16 mmol) was dissolved in 30 mL of ether and cooled to −30° C.; 35 mL of a 1 N solution of lithium aluminum hydride in ether was added at a rate so as to maintain a constant temperature and a modest rate of gas evolution. The mixture was stirred at −30° C. for 10 minutes, and then it was warmed to 0° C. for 1 hour. The reaction was quenched by the careful addition of ethyl acetate (Caution! Vigorous gas evolution) and stirred for 10 minutes, then quenched with a solution of Rochelle's salt. The resultant mixture was partitioned between ethyl acetate and water; the organic phase was washed with brine and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 5% to 30% ethyl acetate in hexanes.

Workup

  1. temperatureto maintain a constant temperature
  2. temperatureit was warmed to 0° C. for 1 hour
  3. customThe reaction was quenched by the careful addition of ethyl acetate (Caution! Vigorous gas evolution)
  4. stirringstirred for 10 minutes
  5. customquenched with a solution of Rochelle's salt
  6. customThe resultant mixture was partitioned between ethyl acetate and water
  7. washthe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. customThe solvents were removed in vacuo
  10. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  11. washeluting with a gradient of 5% to 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-145e01aa6f0d430e94077d7accf22106
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Linked notes

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