Aluminium lithium hydride → (S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

HRID 990398Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([C:14](=[O:19])N(OC)C)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([CH:14]=[O:19])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester (288 mg, 1.0 mmol) was dissolved in Et2O (10 mL), cooled to 0° C., treated with LAH (38 mg, 1.0 mmol), and stirred cold for 30 minutes. The reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O. The reaction was diluted with H2O (100 mL), washed with Et2O (3×100 mL), then the organic layers were combined, washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product which was carried on immediately without further purification.

Workup

customThe reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O
additionThe reaction was diluted with H2O (100 mL)
washwashed with Et2O (3×100 mL)
washwashed with saturated bicarbonate solution and brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5309e48acc1d49b89c642ed76a99e323
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06458781B1

Reaction notes

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