Malonic Acid → HCID 18694318, compound

HRID 1870873Notes

Reaction equation

HRID 1870873 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[N:15](C)[CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.ClC(OC(Cl)C)=O.[C:24]([OH:30])(=[O:29])[CH2:25][C:26]([OH:28])=[O:27]>C(O)(C)C>[C:24]([OH:30])(=[O:29])[CH2:25][C:26]([OH:28])=[O:27].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[NH:15][CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 5213051-Chloroethyl chloroformateHCID 9859239HCID 9859239, compound

Product 1

HCID 18694318HCID 18694318, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound was prepared from (±)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene (1.6 g, 7.37 mmol) and 1-chloroethyl chloroformate (1.2 mL, 1.6g, 11 mmol). The free base of the title compound was dissolved in isopropanol and added malonic acid (0.43 g, 4.1 mmol), the title compound precipitated from this solution and was isolated by filtration. Yield 1.14 g (50%) m.p. 132.2-132.6° C.

Workup

  1. customthe title compound precipitated from this solution
  2. customwas isolated by filtration

Sources & evidence

ORD record
ord-7484b54d898041e89554648839b1390f
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Reaction notes

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