Allyl chloroformate → HCID 178459855, compound

HRID 861376Notes

Reaction equation

HRID 861376 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14]>[OH-].[Na+].O1CCOCC1>[CH2:16]([O:15][C:13]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)=[O:14])[CH:17]=[CH2:18]

Participants

5

Reactant 2

HCID 18052Allyl chloroformateHCID 178511262HCID 178511262, compound

Product 1

HCID 178459855HCID 178459855, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 34.2 g (217.5 mmol) of trans 4-aminomethylcyclohexanecarboxylic acid (Aldrich) in 217 mL of 2M aq. NaOH and 217 mL of dioxane was cooled to 15° C. To this solution was added 25 mL (235 mmol) of allyl chloroformate (Aldrich) in a slow stream. After the addition, the cold bath was removed, and the solution was stirred overnight at ambient temperature. The reaction mixture was poured slowly into a rapidly stirred mixture of 1L of 1M aq. citric acid and ice. The resulting mixture was stirred for 0.5 h and the precipitate collected by filtration, washed with water, and dried to a constant weight of 49.3 g (94%) of the title compound as a colorless solid.

Workup

  1. additionAfter the addition
  2. customthe cold bath was removed
  3. additionThe reaction mixture was poured slowly into a rapidly stirred mixture of 1L of 1M aq. citric acid and ice
  4. stirringThe resulting mixture was stirred for 0.5 h
  5. filtrationthe precipitate collected by filtration
  6. washwashed with water
  7. dry with materialdried to a constant weight of 49.3 g (94%) of the title compound as a colorless solid

Sources & evidence

ORD record
ord-f008098fc94142d7b66d06c8d925b095
Source dataset
uspto-grants-1998_02
Patent number
US05714485

Reaction notes

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