Methylhydrazine → Tert-butyl 3-(aminooxy)piperidine-1-carboxylate

HRID 1821821Notes

Reaction equation

HRID 1821821 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.CNN>>[NH2:3][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 68981003tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 68983062Tert-butyl 3-(aminooxy)piperidine-1-carboxylateYield 73%

Procedure

Deprotection of tert-butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]piperidine-1-carboxylate with methylhydrazine following the procedure described for the preparation of Reference Example 9 gave tert-butyl 3-(aminooxy)piperidine-1-carboxylate (1.0 g, 73%) as an off-white, waxy solid: 1H NMR (500 MHz, CDCl3) δ 1.34-1.39 (1H, m), 1.47 (9H, s), 1.69-1.76 (3H, m), 3.12-3.26 (1.5H, m), 3.45-3.60 (3H, m), 3.77-3.83 (0.5H, m), 3.37-5.47 (2H, m).

Sources & evidence

ORD record
ord-f96068bfe72c476faee84328bc9fdb87
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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