Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate → tert-Butyl 3-((1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1751018Notes

Reaction equation

HRID 1751018 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([CH:39]=[CH:40][CH:41]=1)[CH2:11][N:12]1[C:16](=[O:17])[C:15]2([CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)[N:14]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[CH:33]1([N:14]2[C:15]3([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:16](=[O:17])[N:12]([CH2:11][C:10]3[CH:9]=[C:8]([CH:41]=[CH:40][CH:39]=3)[C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13]2)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

4

Reactant 1

HCID 58046810Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58046813tert-Butyl 3-((1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 3-(3-(tert-butoxycarbonyl)benzyl)-1-cyclohexyl-4-oxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.37 g, 2.44 mmol) and palladium on carbon (10 wt. %, wet, Degussa type E101 NE/W,) (0.27 g) in ethyl acetate (20 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 a foam (1.04 g, quant.); MS for C25H37N3O3 m/z 428 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-47e6574805f441ed83ff172c37bee4d4
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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