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

HRID 1751055Notes

Reaction equation

HRID 1751055 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:39]=[CH:40][CH:41]=1)[CH2:14][N:15]1[C:19](=[O:20])[C:18]2([CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[N:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl.O1CCOCC1>[O:20]=[C:19]1[C:18]2([CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[N:17]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:16][N:15]1[CH2:14][C:13]1[CH:12]=[C:11]([CH:41]=[CH:40][CH:39]=1)[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 1

HCID 66652022Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 58046631Benzyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 99.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (913 mg, 1.646 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 4-5 h. The mixture was concentrated in vacuo and the residue was lyophilized to afford the hydrogen chloride salt of the title compound as a cream solid (747 mg, quant); MS for C28H29N3O3 m/z 456.04 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-c61751cecaa24639a60c49363ad9a374
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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