N-Hydroxyphthalimide → (S)-4-(aminooxy)-2-(tert-butyldimethylsilyloxy)butanamide

To a solution of (S)-2-(tert-butyldimethylsilyloxy)-4-hydroxybutanamide (4.85 g, 20.8 mmol) in CH2Cl2 (150 mL) was added 2-hydroxyisoindoline-1,3-dione (5.1 g, 31.2 mmol) and triphenylphosphine (8.2 g, 31.2 mmol). The resultant mixture was cooled to 0° C. and diisopropyl azodicarboxylate (6.0 ml, 31.2 mmol) was slowly added dropwise with an addition funnel under N2 atmosphere. The reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was concentrated to provide clear oil, which was purified by flash chromatography (60% EtOAc—Hexane). The resultant pale yellow compound was dissolved in CH2Cl2 (60 ml). Hydrazine hydrate (670 μL, 8.8 mmol) was added. The reaction mixture was stirred at ambient temperature for 8 h. The resultant solid was filtered off and the filtrate concentrated under reduced pressure to provide a clear yellow oil of (S)-4-(aminooxy)-2-(tert-butyldimethylsilyloxy)butanamide (1.1 g, 4.4 mmol). [M+H] calc'd for C10H24N2O3Si, 249; found, 249.

1. concentrationThe reaction mixture was concentrated
2. customto provide clear oil, which
3. customwas purified by flash chromatography (60% EtOAc—Hexane)
4. dissolutionThe resultant pale yellow compound was dissolved in CH2Cl2 (60 ml)
5. stirringThe reaction mixture was stirred at ambient temperature for 8 h
6. filtrationThe resultant solid was filtered off
7. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-d84b108248e64302be03338503f2cd7f

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618290B2