Aluminium lithium hydride → HCID 69284672, compound

HRID 566884Notes

Reaction equation

HRID 566884 reaction equation
[CH3:1][C:2]([Si:5]([CH3:33])([CH3:32])[O:6][CH2:7][C@@H:8]([CH3:31])[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]([C:17]([CH3:30])([CH3:29])[C:18](=[O:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:3][C:2]([Si:5]([CH3:32])([CH3:33])[O:6][CH2:7][C@@H:8]([CH3:31])[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]([C:17]([CH3:30])([CH3:29])[C@@H:18]([OH:28])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)([CH3:1])[CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57114671HCID 57114671, compound

Product 1

HCID 69284672HCID 69284672, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

iv)—A solution of the ketone 5 (140 g) obtained in the previous step in dry tetra-hydrofuran (1400 ml) was added in 30 min. to an ice-cooled suspension of lithium aluminium hydride (35 g) in tetrahydrofuran (1750 ml). After stirring of the mixture for 1 h at room temperature, the reaction was quenched by addition of a saturated aqueous solution of sodium sulfate (152 ml), followed by water (39 ml). Ethyl acetate (1750 ml) was added, and the mixture was filtered over celite. The filtrate was concentrated under reduced pressure to give (3β,20S)-21-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4,20-trimethylpregn-5-en-3-ol (6) (136.3 g), which was used in the following step without further purification.

Workup

  1. temperaturecooled
  2. customthe reaction was quenched by addition of a saturated aqueous solution of sodium sulfate (152 ml)
  3. additionEthyl acetate (1750 ml) was added
  4. filtrationthe mixture was filtered over celite
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-620745119a5147ca9a5c3b21418cc3fd
Source dataset
uspto-grants-2001_01
Patent number
US06177420B1

Reaction notes

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