(R)-tert-butyl 1-(4-nitrophenyl)ethylcarbamate → (R)-[1-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 2093025Notes

Reaction equation

HRID 2093025 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 57584601(R)-tert-butyl 1-(4-nitrophenyl)ethylcarbamate

Product 1

HCID 10633571(R)-[1-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of C1 (1.0 g, 3.8 mmol) in MeOH (20 mL) was charged to a Parr reactor, and the contents of the reactor were treated with 10% Pd/C (800 mg, 0.376 mmol). The contents of the reactor were then hydrogenated at 45 Psi hydrogen pressure and 25° C. for 4 hours. The contents of the reactor were filtered through Celite® and washed with DCM. The combined filtrates were concentrated to provide C2 as a sticky orange residue. Yield: 690 mg, 78% yield. GC MS=236. 1H NMR (500 MHz, d6-DMSO) δ: 7.07 (d, 1H), 6.88 (d, 2H), 6.43 (d, 2H), 4.85 (s, 2H), 4.40 (m; 1H), 1.31 (s, 9H), 1.18 (d, 3H).

Workup

  1. filtrationThe contents of the reactor were filtered through Celite®
  2. washwashed with DCM
  3. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-b7d1764a03234201a7ba42968fafb2ca
Source dataset
uspto-grants-2013_05
Patent number
US08440822B2

Reaction notes

Loading…