Ethyl formimidate hydrochloride → 1-(Iminomethyl)piperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)-ethanoate Monohydrochloride

HRID 458736Notes

Reaction equation

HRID 458736 reaction equation
[F:1][C:2]1([F:25])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[C:8]([O:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[O:9])[CH2:3]1.[ClH:26].[CH:27](=[NH:31])OCC>C(O)C>[ClH:26].[F:25][C:2]1([F:1])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:24])([C:17]2[CH:18]=[CH:19][C:20]([Br:23])=[CH:21][CH:22]=2)[C:8]([O:10][CH:11]2[CH2:12][CH2:13][N:14]([CH:27]=[NH:31])[CH2:15][CH2:16]2)=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 12578842Ethyl formimidate hydrochlorideHCID 69766871piperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoate

Product 1

HCID 697673051-(Iminomethyl)piperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)-ethanoate MonohydrochlorideYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 13 mg of piperidin-4-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-(4-bromophenyl)ethanoate in 1 ml of anhydrous ethanol, 4 mg of ethyl formimidate hydrochloride was added, followed by 13 hours' stirring at room temperature. The reaction liquid was condensed to dry solid. Purifying the crude product on silica gel column chromatography (eluent: chloroform/methanol=10/1), 9 mg of the title compound was obtained as a colorless solid.

Workup

  1. customThe reaction liquid
  2. customcondensed
  3. customto dry solid
  4. customPurifying the crude product on silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-642460f67c7e4223a5e21d1acd8c7467
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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