N-(tert-Butoxycarbonyl)-L-leucine methyl ester → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate
Reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>C1(C)C=CC=CC=1>[C:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=[O:2])=[O:7])([CH3:12])([CH3:11])[CH3:10]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Under an argon gas stream, N-(tert-butoxycarbonyl)-L-leucine methyl ester (0.98 g, 4.0 mmol) was dissolved in toluene (7.1 ml), and cooled to -78° C. To the reaction solution, while keeping the temperature at -60 to -70° C., was added gradually aluminum diisobutyl hydride (toluene 1.0 M solution, 5.0 ml). After stirring at -78° C. for 30 minutes, thereby there was obtained (S)-2-(tert-butoxycarbonylamino)-4-methylpentanal.
Workup
- customat -60 to -70° C.
Sources & evidence
- ORD record
- ord-acf2207d36a84b33a7f222ba9009a12e
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06066672
Reaction notes
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