Triethylamine → 5-Aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester 6-[2-(7-bromo-dibenzofuran-3-yl)-2-oxo-ethyl]ester

HRID 1185958Notes

Reaction equation

HRID 1185958 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:17]([C:18]([OH:20])=[O:19])[CH2:16][C:13]2([CH2:15][CH2:14]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:29][C:30]([C:32]1[CH:33]=[CH:34][C:35]2[C:39]3[CH:40]=[CH:41][C:42]([Br:44])=[CH:43][C:38]=3[O:37][C:36]=2[CH:45]=1)=[O:31]>C(#N)C.CN(C=O)C>[Br:44][C:42]1[CH:41]=[CH:40][C:39]2[C:35]3[CH:34]=[CH:33][C:32]([C:30](=[O:31])[CH2:29][O:19][C:18]([CH:17]4[CH2:16][C:13]5([CH2:14][CH2:15]5)[CH2:12][N:11]4[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[O:20])=[CH:45][C:36]=3[O:37][C:38]=2[CH:43]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 596105415-[(Benzyloxy)carbonyl]-5-azaspiro[2.4]heptane-6-carboxylic acidHCID 59610886HCID 59610886, compound

Product 1

HCID 666211095-Aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester 6-[2-(7-bromo-dibenzofuran-3-yl)-2-oxo-ethyl]esterYield 95.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To the solution of (s) 5-aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester (138 mg, 0.5 mmol) and triethylamine (65 μl, 0.47 mmol) in acetonitrile (3 ml) was added slowly a solution of 2-bromo-1-(7-bromo-dibenzofuran-3-yl)-ethanone (143 mg, 0.39 mmol) in DMF (4 ml). The mixture was stirred for 12 hours, and the solvent was evaporated. The mixture was diluted with EtOAc, and washed with 1.0 N NaOH solution, water and brine, and was dried with sodium sulfate. Concentration gave 5-Aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester 6-[2-(7-bromo-dibenzofuran-3-yl)-2-oxo-ethyl]ester (210 mg)

Workup

  1. customthe solvent was evaporated
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with 1.0 N NaOH solution, water and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-ea007dadbc3746ed9c632f493a634582
Source dataset
uspto-grants-2014_03
Patent number
US08669234B2

Reaction notes

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