1,1-Dimethylethyl 3-[(4-nitrophenyl)methyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → HCID 58046774, compound

HRID 1751137Notes

Reaction equation

HRID 1751137 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]2[C:13](=[O:14])[C:12]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:13](=[O:14])[C:12]3([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[N:11]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:10]2)=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 151213361,1-Dimethylethyl 3-[(4-nitrophenyl)methyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58046774HCID 58046774, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-(4-nitrobenzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (2.59 g, 5.55 mmol) and palladium on carbon (10 wt. %, wet, Degussa type E101 NE/W) (0.52 g) in ethyl acetate (30 mL) was stirred at room temperature under hydrogen (balloon) for 3 hours. The catalyst was removed by filtration and the filtrate evaporated and dried under vacuum to give product as an oil (2.42 g, quant.); 1H NMR (DMSO-d6); δ1.45 (s, 9H); 1.57 (d, J=14 Hz, 2H); 2.39 (m, 2H); 3.45 (m, 2H); 3.88 (m, 2H); 4.36 (s, 2H); 4.52 (s, 2H); 5.09 (s, 2H); 6.53 (m, 2H); 6.64 (d, J=8 Hz, 2H); 6.75 (t, J=7.6 Hz, 1H); 6.96 (d, J=8.4 Hz, 2H); 7.16 (dd, J=7.2 Hz and 8.8 Hz, 2H); MS for C25H32N4O3 m/z 437 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-db1d785847974fe1bc21fab8d02770cc
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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