Diethyl Ether → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 22450

Reaction equation

HRID 22450 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CON(C)[C:10](=[O:24])[C@H:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].S([O-])(O)(=O)=O.[K+].CCOCC>O>[C:16]([O:15][C:13]([NH:12][C@H:11]([CH:10]=[O:24])[CH2:20][CH:21]([CH3:22])[CH3:23])=[O:14])([CH3:18])([CH3:19])[CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 516920Potassium bisulfateHCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium aluminum hydride (2.5 equiv.) is added to a stirred solution of compound (7). Reduction is complete within 15-20 minutes. The mixture is hydrolyzed with a solution of potassium hydrogen sulfate in water. Ether is added and the aqueous phase is separated and extracted. The organic phases are combined, washed with 1N HCl saturated sodium hydrogen carbonate and saturated sodium chloride, and dried with magnesium sulfate. The solvent is evaporated to leave the desired product

Workup

  1. customthe aqueous phase is separated
  2. extractionextracted
  3. washwashed with 1N HCl saturated sodium hydrogen carbonate and saturated sodium chloride
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-c05cdbbfbba14f20a453eb4c70efeaa1
Source dataset
uspto-grants-1995_06
Patent number
US05428019

Linked notes

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