Water → HCID 70049825, compound

HRID 1757166Notes

Reaction equation

HRID 1757166 reaction equation
[F:1][C:2]1[C:3]([O:25][CH3:26])=[C:4]([CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:5][C@H:6]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:9][NH:8][CH2:7]1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].O>C(Cl)(Cl)Cl>[C:34]([N:8]1[CH2:9][C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[C@H:6]([CH2:5][C:4]2[CH:21]=[C:22]([F:24])[CH:23]=[C:2]([F:1])[C:3]=2[O:25][CH3:26])[CH2:7]1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 70048414HCID 70048414, compound

Product 1

HCID 70049825HCID 70049825, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.17 g (6.17 mmol) of trans-3-(3,5-difluoro-2-methoxybenzyl)-4-(3,4-dimethoxyphenyl)pyrrolidine prepared in step (13) of Example 4 was dissolved in 30 ml of chloroform, and 0.75 g (7.4 mmol) of triethylamine was added thereto. 10 ml of a solution of 0.5 ml (7.0 mmol) of acetyl chloride in chloroform was dropwise added thereto under cooling with ice, and the mixture was stirred at room temperature for 3 hr. 1 ml of water was added thereto to stop the reaction. The reaction mixture was washed with water, a 2N hydrochloric acid solution, and a saturated aqueous sodium hydrogencarbonate solution sequentially, and dried over anhydrous sodium sulfate. The solvent was distilled off in vacuo, and the residue was subjected to silica gel column chromatography (methylene chloride:methanol=97:3) to prepare 2.5 g (quantitative) of the intended product.

Workup

  1. temperatureunder cooling with ice
  2. customthe reaction
  3. washThe reaction mixture was washed with water
  4. dry with materiala 2N hydrochloric acid solution, and a saturated aqueous sodium hydrogencarbonate solution sequentially, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off in vacuo
  6. customto prepare 2.5 g (quantitative) of the intended product

Sources & evidence

ORD record
ord-9889687f6e8c4784bc6dfffc716dbf03
Source dataset
uspto-grants-1995_08
Patent number
US05444083

Reaction notes

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