Diisopropylethylamine → 7-(tert-Butyl) 5-Methyl (6S,7S)-6-(4-Phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-5,7-dicarboxylate

HRID 1664622Notes

Reaction equation

HRID 1664622 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]([C@@H:15]3[C@@H:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][C:18]4([CH2:20][CH2:19]4)[CH2:17][NH:16]3)=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(OCC)C>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([C:13]([C@@H:15]3[C@@H:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][C:18]4([CH2:19][CH2:20]4)[CH2:17][N:16]3[C:23]([O:25][CH3:26])=[O:24])=[O:14])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 67006279tert-butyl (6S,7S)-6-(4-phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-7-carboxylate

Product 1

HCID 866302677-(tert-Butyl) 5-Methyl (6S,7S)-6-(4-Phenylpiperazine-1-carbonyl)-5-azaspiro[2.5]octane-5,7-dicarboxylateYield 198.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl chlorofomate (55 μL, 700 μL) was added to a solution of tert-butyl (6S,7S)-6-[(4-phenylpiperazin-1-yl)carbonyl]-5-azaspiro[2.5]octane-7-carboxylate (248.4 mg, 0.62 mmol) and di-isopropylethylamine (0.70 mmol, 0.125 mL) in 5 mL acetonitrile. The mixture was stirred at RT for 3 h. Solvent was removed to afford a residue which was dissolved in ethyl ether (15 mL), washed with water (3×2 mL) and dried over Na2SO4. The solution was filtered and concentrated to afford 281 mg of the 7-tert-butyl 5-methyl (6S,7S)-6-[(4-phenylpiperazin-1-yl)carbonyl]-5-azaspiro[2.5]octane-5,7-dicarboxylate.

Workup

  1. customSolvent was removed
  2. customto afford a residue which
  3. washwashed with water (3×2 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8572a6e0d4042e788304991e37a6383
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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