Benzyl 2-(3-(methoxycarbonyl)benzyl)-1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate → Methyl 3-((1-oxo-4-phenyl-2,8-diazaspiro[4.5]decan-2-yl)methyl)benzoate

HRID 1751033Notes

Reaction equation

HRID 1751033 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][N:9]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2([CH2:24][CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][CH2:20]2)[C:10]1=[O:35])=[O:4]>Cl.O1CCOCC1>[O:35]=[C:10]1[C:11]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][N:9]1[CH2:8][C:7]1[CH:6]=[C:5]([CH:38]=[CH:37][CH:36]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 66652195Benzyl 2-(3-(methoxycarbonyl)benzyl)-1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652428Methyl 3-((1-oxo-4-phenyl-2,8-diazaspiro[4.5]decan-2-yl)methyl)benzoateYield 105.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl 2-(3-(methoxycarbonyl)benzyl)-1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate (1.335 g, 2.79 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 3 h. The mixture was concentrated in vacuo to afford the hydrogen chloride salt of the title compound as a cream powder (1.116 g, 97%); 1H NMR (400 MHz, DMSO-d6): δ 1.11-1.18 (m, 1H); 1.71-1.83 (m, 2H); 1.93-1.97 (m, 1H); 3.38-3.42 (m, 1H); 3.45-3.49 (m, 3H); 3.55-3.59 (m, 2H); 3.65-3.72 (m, 1H); 3.69-3.71 (m, 1H); 3.86 (s, 3H); 4.57 (d, 2H, J=4 Hz); 7.19-7.21 (m, 2H); 7.25-7.33 (m, 3H); 7.53-7.60 (m, 2H); 7.89-7.92 (m, 2H); 8.61 (bs, 1H); 9.07 (bs, 1H); MS for C23H26N2O3 m/z 379.2 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-94212e95099747b59b9e3ce560888efb
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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