Stannous Chloride → HCID 86590289, compound

HRID 895350Notes

Reaction equation

HRID 895350 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N+:35]([O-])=O)[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[CH2:7][CH2:6]1.Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH2:35])[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:16]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 86590290HCID 86590290, compound2×

Product 1

HCID 86590289HCID 86590289, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a round-bottomed flask fitted with a reflux condenser and a thermometer were introduced {4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(2-nitro-phenyl)-ethyl]-piperazin-1-yl}-acetic acid methyl ester (compound 190 prepared at example 1.4.1 above; 2 g, 3.64 mmoles), SnCl2 (3.45 g, 18.2 mmoles) and MeOH (40 ml) and the reaction mixture was heated at 60° C. for 3 hours. MeOH was evaporated in vacuo and the crude was taken up in water. The pH was adjusted to 8-9 by addition of aqueous NaOH and the solution was extracted with AcOEt. The combined organic phases were dried over MgSO4 and concentrated. The resulting oil was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 99/1/0.1 v/v/v) to yield {4-[1-(2-Amino-phenyl)-2-(3,5-bis-trifluoromethyl-benzyloxy)-ethyl]-piperazin-1-yl}-acetic acid methyl ester (compound 323; 1.7 g, 90%) as a yellow oil.

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. customMeOH was evaporated in vacuo
  3. additionThe pH was adjusted to 8-9 by addition of aqueous NaOH
  4. extractionthe solution was extracted with AcOEt
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting oil was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 99/1/0.1 v/v/v)

Sources & evidence

ORD record
ord-388f4da2b34c41eeb6047f106324ac8d
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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