Benzyl 3-(2-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate → Tert-butyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoate

HRID 1751128Notes

Reaction equation

HRID 1751128 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:18](=[O:19])[C:17]2([CH2:24][CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][CH2:20]2)[N:16]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:15]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[O:19]=[C:18]1[C:17]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[N:16]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:15][N:14]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

5

Reactant 1

HCID 58046753Benzyl 3-(2-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58046768Tert-butyl 2-(4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)benzoateYield 102.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-(2-(tert-butoxycarbonyl)phenyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.86 g, 3.44 mmol, 1 equiv) in a mixture of ethyl acetate and ethanol was charged with 10% palladium on carbon (360 mg, 20%/wt) and the resulting mixture was hydrogenated at atmospheric pressure for 16 h. The reaction was filtered over Celite and the filtrate was concentrated and dried in vacuo to afford the title compound as a white foam (1.44 g, 96.4%); 1H NMR (400 MHz, DMSO-d6): δ 1.49 (s, 9H); 1.71 (d, 2H, J=13.2 Hz); 2.41-2.49 (m, 2H); 2.84-2.88 (m, 2H); 3.08-3.13 (m, 2H); 5.07 (s, 2H); 6.78 (t, 1H, J=7.2 and 7.6 Hz); 6.98 (s, 1H); 7.00 (s, 1H); 7.23-7.27 (m, 2H); 7.46-7.49 (m, 1H); 7.60 (dd, 1H, J=1.2 and 1.6 Hz); 7.65-7.69 (m, 1H); 7.77 (dd, 1H, J=1.2 and 1.6 Hz); MS for C24H29N3O3 m/z 408.22 (M+H)+.

Workup

  1. filtrationThe reaction was filtered over Celite
  2. concentrationthe filtrate was concentrated
  3. customdried in vacuo

Sources & evidence

ORD record
ord-33dc130703834b18b59ec06765cd58d4
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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