2-(4-Nitro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester → tert-Butyl 2-(4-aminophenyl)morpholine-4-carboxylate

HRID 387231Notes

Reaction equation

HRID 387231 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 671197592-(4-Nitro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 58315596tert-Butyl 2-(4-aminophenyl)morpholine-4-carboxylateYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(4-nitro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (20 mg, 0.064 mmol) and Pd/C (5%, 2 mg) in methanol was stirred under hydrogen for 24 h. The catalyst was filtered off and washed with methanol. The filtrate was evaporated to give the title compound as an off-white solid (14 mg, 0.050 mmol, 78%). ESMS m/z 223 (M+H-tBu)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.00 (d, J=8.3 Hz, 2H) 6.52 (d, J=8.3 Hz, 2H) 5.04 (s, 2H) 4.15 (dd, J=10.5, 2.5 Hz, 1H) 3.88 (dd, J=11.8, 2.5 Hz, 1H) 3.76 (d, J=12.8 Hz, 2H) 3.48 (td, J=11.7, 2.8 Hz, 1H) 2.92 (br. s., 1H) 2.77 (br. s., 1H) 1.41 (s, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e021e8d4225146b0a474cb863e3a9ff9
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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