tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate → tert-butyl (2R,5S)-2-[2-(2-aminophenyl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

HRID 629697Notes

Reaction equation

HRID 629697 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][C@@H:13](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-])=O)[O:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>FC(F)(F)CO.[OH-].[OH-].[Pd+2]>[NH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][CH2:23][C@H:13]1[O:12][CH2:11][C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14]1

Participants

4

Reactant 1

HCID 86726304tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate

Product 1

HCID 86726305tert-butyl (2R,5S)-2-[2-(2-aminophenyl)ethyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate (1 eq.) in 2,2,2,-trifluoroethanol (0.4 M) at rt was added 20% Pd(OH)2 (0.2 eq.). The reaction was degassed and then shaken under 1 atm of H2 for 24 hrs. The reaction mixture was filtered on celite and concentrated to afford the desired compound.

Workup

  1. customThe reaction was degassed
  2. filtrationThe reaction mixture was filtered on celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-12b84f6356ed422c8729beda30144d06
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

Loading…