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

HRID 1750998Notes

Reaction equation

HRID 1750998 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:33]=[CH:34][CH:35]=1)[CH2:8][N:9]1[C:13](=[O:14])[C:12]2([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)[N:11]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10]1)=[O:4]>Cl.O1CCOCC1>[O:14]=[C:13]1[C:12]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:11]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:10][N:9]1[CH2:8][C:7]1[CH:6]=[C:5]([CH:35]=[CH:34][CH:33]=1)[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 1

HCID 66652862Tert-butyl 3-(3-(methoxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652852Methyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 100.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 3-(3-(methoxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (1.2 g, 2.5 mmol, 1 equiv) in 4M hydrogen chloride solution in dioxane was stirred at ambient temperature for 3 h. The reaction mixture was concentrated and dried in vacuo to afford the hydrogen chloride salt of the title compound as a white powder (0.95 g, quant.); MS for C22H25N3O3 m/z 379.19 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-4d5e48d4550149a7bdf6d835259d6f63
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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