Hydroxylamine → Tert-butyl 3-[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]propanoate

HRID 219884Notes

Reaction equation

HRID 219884 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]([CH3:17])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:2].[NH2:21][OH:22]>C(O)C>[NH2:2][C:1](=[N:21][OH:22])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]([CH3:17])[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66678103tert-Butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate

Product 1

HCID 72307470Tert-butyl 3-[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]propanoateYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 3-[(3-cyanobenzyl)(methyl)amino]propanoate (4.5 g, 0.0164 mol) in ethanol (60 mL) under N2, was added hydroxylamine (2.5 mL, 0.082 mol) in one portion. After being stirred at RT for 12 h, the reaction mixture was concentrated under reduced pressure to afford the title compound as a white gummy solid (4.5 g, 84%). 1H NMR (DMSO-d6, 400 MHz) δ 9.56 (s, 1H), 7.51-7.53 (m, 2H), 7.27-7.31 (m, 2H), 5.74 (s, 2H), 3.44 (s, 2H), 2.55-2.59 (m, 2H), 2.34-2.38 (m, 2H), 2.09 (s, 3H), 1.37 (s, 9H). LC/MS (Method A): 308.2 (M+H)+. HPLC (Method B) Rt 5.18 min (Purity: 96.5%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d355b216a5547d79f4d1e0a4d910a77
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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