Hydroxylamine → HCID 76637589, compound

HRID 1093061Notes

Reaction equation

[C:1]([CH:3]([CH:16]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17]1)[N:4]([CH3:15])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:2].[NH2:23][OH:24]>C(O)C>[NH2:2][C:1](=[N:23][OH:24])[CH:3]([N:4]([CH3:15])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:16]1[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH2:17]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of benzyl cyano(3-(hydroxymethyl)cyclopentyl)methyl(methyl)carbamate (0.540 g, 1.79 mmol) in ethanol (20 mL) was added 50% aqueous solution of hydroxylamine (0.07 mL, 2.15 mmol). The reaction mixture was stirred at 60° C. for 18 hours. The solvent was removed in vacuo to afford 0.610 g (76% yield) of title compound 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.43 (5 H, m), 7.14-7.23 (2 H, m), 5.18 (2 H, br s), 4.87-4.93 (1 H, m), 4.24 (1 H, m), 3.49-3.60 (2 H, m), 2.83-2.94 (3 H, br s), 2.60-2.71 (1 H, m), 2.11-2.49 (2 H, m), 1.60-2.11 (3 H, m), 1.25-1.55 (2 H, m). (+ESI, M+H+) 2 peaks m/z 336.

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5e6204a0270e491cafd1540c4018ed34
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129398B2

Reaction notes

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