Methylhydrazine → tert-Butyl 4-(aminooxy)piperidine-1-carboxylate

HRID 1821819Notes

Reaction equation

HRID 1821819 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.CNN>>[NH2:3][O:12][CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 24729482tert-Butyl 4-(aminooxy)piperidine-1-carboxylateYield 73%

Procedure

Deprotection of tert-butyl 4-[(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 4-(aminooxy)piperidine-1-carboxylate (1.3 g, 73%) as an amber oil: 1H NMR (500 MHz, CDCl3) δ 1.47 (9H, s), 1.48-1.54 (2H, m), 1.86-1.88 (2H, m), 3.04-3.10 (2H, m), 3.66-3.69 (2H, m), 4.20 (1H, br s), 5.30 (2H, br s).

Sources & evidence

ORD record
ord-3c6ea8a2ec1d4732863e68ef36f8a150
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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