Methylhydrazine → (S)-O-(2-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamine

HRID 78998Notes

Reaction equation

[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@@H:7]([CH3:21])[CH2:8][O:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>C(Cl)Cl>[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][C@@H:7]([CH3:21])[CH2:8][O:9][NH2:10])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold solution of crude 2-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-propoxy]-isoindole-1,3-dione (0.28 mol) in DCM (200 ml) at 0° C. was added methyl hydrazine (14.74 mol, 0.28 mol). The reaction mixture was stirred at 0° C. for 30 minutes then filtered and the filtrate concentrated in vacuo. The resultant residue was subjected to distillation (b.p. 108-112° C. at 2-10 mbar) to yield the title compound as a colourless oil. (42.63 g, 74% from ethyl lactate). 1H NMR (CDCl3, 400 MHz) 5.36 (2H, s), 3.95 (1H, m), 3.55-3.41 (2H, m), 1.04 (3H, d, J=6.28 Hz), 0.81 (9H, s), 0.02 (6H, m).

Workup

filtrationthen filtered
concentrationthe filtrate concentrated in vacuo
distillationThe resultant residue was subjected to distillation (b.p. 108-112° C. at 2-10 mbar)

Sources & evidence

ORD record: ord-aefdebc9b87a48feb766b20b01ee5bb1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841462B2

Reaction notes

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