Aluminium lithium hydride → HCID 69031225, compound

HRID 1867225Notes

Reaction equation

HRID 1867225 reaction equation
[CH3:1][C@H:2]1[CH2:8][C:7](=[O:9])[C@@:4]2([O:6][CH2:5]2)[C:3]21[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:5][C@@:4]1([OH:6])[C:3]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C@@H:2]([CH3:1])[CH2:8][C@@H:7]1[OH:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86622551HCID 86622551, compound

Product 1

HCID 69031225HCID 69031225, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(3R*,11S*)-11-Methyl-1-oxadispiro[2.0.6.3]tridecan-13-one (800 mg, 3.84 mmol) was reduced with lithium aluminum hydride (440 mg, 11.5 mmol) in Et2O (2 mL+4 mL) at ambient temp. for 16 h. Quenching with water (5 mL) and aq. HCl (5 N, 5 mL), usual extraction and purification by silica-gel FC (pentane/Et2O, 2:1, Rf=0.16) furnished (1R*,2R*,4S*)-/(1R*,2S*,4S*)-1,4-dimethylspiro[4.6]undecane-1,2-diol (620 mg, 76%).

Workup

  1. customQuenching with water (5 mL) and aq. HCl (5 N, 5 mL), usual extraction and purification by silica-gel FC (pentane/Et2O, 2:1, Rf=0.16)

Sources & evidence

ORD record
ord-307e45c01660437ca4a01abd8b9e518b
Source dataset
uspto-grants-2009_12
Patent number
US07632791B2

Reaction notes

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