Diiodomethane → 1-tert-Butoxycarbonyl-2(S)-(2-cyclopropyloxyethyl)-4-(1-naphthoyl)piperazine

HRID 1598479Notes

Reaction equation

HRID 1598479 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH:29]=[CH2:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:32]I.C([Zn]CC)C>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:26][CH2:27][O:28][CH:29]1[CH2:32][CH2:30]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 228841371-tert-Butoxycarbonyl-2(S)-(2-vinyloxyethyl)-4-naphthoylpiperazineHCID 178418750HCID 178418750, compound

Product 1

HCID 228841291-tert-Butoxycarbonyl-2(S)-(2-cyclopropyloxyethyl)-4-(1-naphthoyl)piperazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-tert-Butoxycarbonyl-2(S)-(2-vinyloxyethyl)-4-naphthoylpiperazine (0.107 g, 0.261 mmol) was dissolved in ether (5 mL) under an argon atmosphere. To this solution was added diiodomethane (0.042 mL, 0.522 mmol) and diethylzinc (0.39 mL, 1M in hexane, 0.39 mmol). The reaction was refluxed for 1 h. The reaction was quenched with water, and extracted with ethyl acetate. The organic extracts were washed with water, saturated sodium chloride, and dried over magnesium sulfate. The title compound was obtained as an oil.

Workup

  1. temperatureThe reaction was refluxed for 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with water, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-a4d12b23dec64b89912942c36fdbdeac
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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