HCID 54228599, compound → HCID 54400228, compound

HRID 2288032Notes

Reaction equation

HRID 2288032 reaction equation
[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[C:16](=[CH:21][C:22]([O:24]CC)=[O:23])[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1>Cl.C(O)(=O)C>[CH:1]1([C:4]([CH:6]([N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[C:16](=[CH:21][C:22]([OH:24])=[O:23])[CH2:15]2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[F:13])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 54228599HCID 54228599, compound

Product 1

HCID 54400228HCID 54400228, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

In a mixture of 75 ml of concentrated hydrochloric acid and 180 ml of acetic acid, 9.72 g (26.9 mmol) of 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-3-ethoxycarbonylmethylidene-4-hydroxypiperidine were dissolved and the resulting solution was allowed to stand at room temperature for 7 days. The reaction mixture was concentrated to dryness under reduced pressure, followed by chromatography on a silica gel column (eluting solvent: chloroform/methanol=100/3~2/1), whereby 5.11 g (yield: 57%) of 1-(α-cyclopropylcarbonyl-2-fluorobenzyl)-3-carboxymethylidene-4-hydroxypiperidine were obtained.

Workup

  1. dissolutionwere dissolved
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  3. washfollowed by chromatography on a silica gel column (eluting solvent: chloroform/methanol=100/3~2/1)

Sources & evidence

ORD record
ord-5e2bd33a90e1472cbb55184344a4a667
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

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