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

HRID 1477392Notes

Reaction equation

HRID 1477392 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[C:6]1([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C@@H:20]3[C@@H:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][C:23]4([CH2:25][CH2:24]4)[CH2:22][NH:21]3)=[O:19])[CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(OCC)C>[C:6]1([N:12]2[CH2:13][CH2:14][N:15]([C:18]([C@@H:20]3[C@@H:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:26][C:23]4([CH2:24][CH2:25]4)[CH2:22][N:21]3[C:2]([O:4][CH3:5])=[O:3])=[O:19])[CH2:16][CH2:17]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 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-dicarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Methyl chloroformate (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-69580a52110647b295135762eab871ed
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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