Diphosgene → HCID 66870786, compound

HRID 1432353Notes

Reaction equation

HRID 1432353 reaction equation
FC(F)(F)[C:3]([O-])=[O:4].[OH:8][C@H:9]1[CH2:14][NH:13][C@@H:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1.O=C(Cl)OC(Cl)(Cl)Cl>ClCCl>[O:4]=[C:3]1[N:13]2[CH2:14][C@H:9]([CH2:10][CH2:11][C@@H:12]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[O:8]1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 84468TrifluoroacetateHCID 66870407HCID 66870407, compound

Product 1

HCID 66870786HCID 66870786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.802 g (2.034 mmoles) of the trifluoroacetate of cis(4-nitrophenyl)methyl 5-hydroxy-2-piperidinecarboxylate (described in Rec. Trav. Chim. (1959), 78, 648-658), of molecular formula C13H16N2O5,CF3CO2H (M=394.303 g) is introduced under a nitrogen atmosphere, into 40 ml of dichloromethane and the reaction medium is cooled down to 0° C. 0.135 ml of diphosgene is added. Agitation is carried out for 15 minutes at 0° C., the temperature is left to rise to ambient temperature and agitation is continued for 35 minutes.

Workup

  1. waitthe temperature is left
  2. customto rise to ambient temperature
  3. waitagitation is continued for 35 minutes

Sources & evidence

ORD record
ord-d91fabb7d6024ba8b40ffb239a736bf7
Source dataset
uspto-grants-2009_11
Patent number
US07612087B2

Reaction notes

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