Benzyl 3-(4-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → Tert-butyl 4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

HRID 1751132Notes

Reaction equation

HRID 1751132 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[C:17]3([CH2:24][CH2:23][N:22](C(OCC4C=CC=CC=4)=O)[CH2:21][CH2:20]3)[N:16]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:15]2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C.CO>[O:19]=[C:18]1[C:17]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:16]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:15][N:14]1[C:11]1[CH:10]=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:13][CH:12]=1

Participants

5

Reactant 1

HCID 58046610Benzyl 3-(4-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58046644Tert-butyl 4-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoateYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 3-(4-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.62 g, 1.14 mmol) and palladium on carbon (10 wt. %, wet, Degussa type E101 NE/W,) (0.12 g) in ethyl acetate (5 mL) and methanol (5 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 foam (0.46 g, quant.); MS for C24H29N3O3 m/z 408 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-375b17e0e08540279898cd5102393ca6
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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