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

HRID 2362960
Notes
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Reaction equation

HRID 2362960 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:8][CH2:7]2)[CH:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][NH:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CCCC1.Br[CH2:44][C:45]1[CH:46]=[C:47]([CH:52]=[CH:53][CH:54]=1)[C:48]([O:50][CH3:51])=[O:49]>CN(C)C=O.C(OCC)(=O)C>[CH3:51][O:50][C:48]([C:47]1[CH:46]=[C:45]([CH:54]=[CH:53][CH:52]=1)[CH2:44][N:3]1[CH2:4][CH:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:8][CH2:7]2)[C:2]1=[O:1])=[O:49]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 517981Methyl 3-(bromomethyl)benzoateHCID 2733832Lithium hexamethyldisilazaneHCID 66652187Benzyl 1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 66652195Benzyl 2-(3-(methoxycarbonyl)benzyl)-1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl 1-oxo-4-phenyl-2,8-diazaspiro[4.5]decane-8-carboxylate (1 g, 3.03 mmol, 1 equiv), lithium bis(trimethylsilyl)amide, 1M in tetrahydrofuran (3.33 ml, 3.33 mmol, 1.1 equiv), and methyl 3-(bromomethyl)benzoate (694.08 g, 3.03 mmol, 1 equiv) in N,N-dimethylformamide was stirred for 16 h at ambient temperature. Reaction was diluted with ethyl acetate and the organic layer was washed with water and brine. The combined organic layers were dried over MgSO4 and concentrated in vacuo. The crude residue was purified using the Biotage flash chromatography system (SNAP 100 g cartridge, Rf=0.6, gradient—10%-50% ethyl acetate in hexanes) to afford the title compound as a cream solid (1.34 g, 92%); 1H NMR (400 MHz, DMSO-d6): δ 0.87-0.92 (m, 1H); 1.33 (s, 9H); 1.46-1.51 (m, 2H); 1.54-1.65 (m, 1H); 3.03-3.07 (m, 1H); 3.34-3.40 (m, 3H); 3.46-3.48 (m, 1H); 3.57-3.61 (m, 1H); 3.69-3.71 (m, 1H); 3.86 (s, 3H); 4.56 (s, 2H); 7.14-7.16 (m, 2H); 7.20-7.28 (m, 3H); 7.52-7.59 (m, 2H); 7.89-7.91 (m, 2H); MS for C31H32N2O5 m/z 513.23 (M+H)+.

Workup

  1. customReaction
  2. washthe organic layer was washed with water and brine
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified

Sources & evidence

ORD record
ord-8f6bacabb4e8402eb5971510cbc8386e
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691836B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes