Ethyl Acetate → 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-propane-1,3-diol hydrochloride salt

HRID 902629Notes

Reaction equation

HRID 902629 reaction equation
C[O:2][C:3](=O)[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[C:35]=2[Cl:44])[CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1)[C:5](O)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C(OCC)C.[Cl-].[Na+].O>[ClH:44].[Cl:44][C:35]1[C:36]([C:40]([F:41])([F:42])[F:43])=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:18]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:17][CH2:16][CH2:15][O:14][C:10]1[CH:9]=[C:8]([CH:4]([CH2:3][OH:2])[CH2:5][OH:6])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 692536562-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-malonic acid monomethyl ester

Product 1

HCID 692526452-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-propane-1,3-diol hydrochloride salt

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-malonic acid monomethyl ester (22 mg, 0.03 mmol) in diethyl ether (1 ml) was added lithium aluminum hydride (100 uL) at 0° C. The reaction was allowed to warm to room temperature before the addition of brine and ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give the title compound free amine as an oil. MS m/e 598.2(M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M). The suspension was evaporated and dried to give the title compound as a white solid (2 mg, 10%).

Workup

  1. dry with materialThe combined organic layers were dried over magnesium sulfate
  2. customevaporated
  3. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

Sources & evidence

ORD record
ord-04e1d3307ccd4df684be57520859a6cb
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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