Aluminium lithium hydride → HCID 54103979, compound

HRID 1779948Notes

Reaction equation

HRID 1779948 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C@H:9]2[C:10](=[O:37])[CH2:11][C@H:12]3[C@:34]([CH3:35])([C@@H:8]12)[C@@H:33]1[C@H:15]([C@H:16]2[C@:30]([CH3:36])([CH2:31][CH2:32]1)[C@H:19]1[C@@H:20]([C@:22]4([O:29][CH2:28][C@H:26]([CH3:27])[CH2:25][CH2:24]4)[O:23][C@H:18]1[CH2:17]2)[CH3:21])[CH2:14][CH2:13]3>C1COCC1>[OH:7][C@@H:8]1[C@@:34]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:36])[C@H:16]3[CH2:17][C@@H:18]3[O:23][C@@:22]4([O:29][CH2:28][C@H:26]([CH3:27])[CH2:25][CH2:24]4)[C@@H:20]([CH3:21])[C@@H:19]32)[CH2:11][C@@H:10]([OH:37])[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 86750803HCID 86750803, compound

Product 1

HCID 54103979HCID 54103979, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.43 g, 15.38 mmol) was added to a solution of (1α,2α,5α,25R)-1,2-epoxy-spirostan-3-one in THF (20 mL) at 0° C. The reaction was gradually warmed to room temperature and after 3 hours, additional lithium aluminum hydride (0.10 g, 3.58 mmol) was added. After 1 hour, the reaction was cooled to 0° C. and quenched by the sequential addition of H2O (0.75 mL), 15% NaOH (0.75 mL), and H2O (1.50 mL). The mixture was dried with MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (50% EtOAc/50% hexane to 95% EtOAc/5%MeOH) to afford 0.460 g, (34%) of the title compound.

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched by the sequential addition of H2O (0.75 mL), 15% NaOH (0.75 mL), and H2O (1.50 mL)
  3. dry with materialThe mixture was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash chromatography (50% EtOAc/50% hexane to 95% EtOAc/5%MeOH)

Sources & evidence

ORD record
ord-f99dba9f249b42008c406529a2fe053a
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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