2-Trimethylsilanylethyl (3-benzyloxy-4-nitrophenoxy)acetate → 2-Trimethylsilanylethyl (4-amino-3-benzyloxyphenoxy)acetate

HRID 660761Notes

Reaction equation

HRID 660761 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[N+:26]([O-])=O)[O:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pt]>[NH2:26][C:25]1[CH:24]=[CH:23][C:11]([O:12][CH2:13][C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:20])[CH3:21])=[O:15])=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 866325882-Trimethylsilanylethyl (3-benzyloxy-4-nitrophenoxy)acetate

Product 1

HCID 866325892-Trimethylsilanylethyl (4-amino-3-benzyloxyphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-trimethylsilanylethyl (3-benzyloxy-4-nitrophenoxy)acetate (5.0 g) and 5% Pt/C (500 mg) in EtOAc (50 mL) is hydrogenated at 1 atm for 3 h. The catalyst is filtered off through Celite and the solvent removed under reduced pressure to afford the title compound: 1H NMR (CDCl3)δ 7.31 (m, 5H), 6.73 (d, J=8.6 Hz, 1H), 6.56 (d, J=2.8 Hz, 1H), 6.29 (dd, J=8.6, 2.8 Hz, 1H), 5.01 (s, 2H), 4.45 (s, 2H), 4.94 (m, 2H), 0.98 (m, 2H), 0.00 (s, 9H).

Workup

  1. filtrationThe catalyst is filtered off through Celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bc0cfb333b894113b3b146be2c6ce599
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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