Dichloromethane → HCID 70066037, compound

HRID 365326Notes

Reaction equation

HRID 365326 reaction equation
OC[C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][CH:9]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)OC1CCCCO1.C(N([CH2:30][CH3:31])CC)C.CS(Cl)(=O)=O.Cl[CH2:38][Cl:39]>>[Cl:39][C@H:38]1[CH2:6][CH2:7][CH2:3][N:4]([CH2:8][CH:9]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:31]2[CH2:30][CH2:18][CH2:19][CH2:20][O:23]2)[CH2:5]1

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70062419HCID 70062419, compound

Product 1

HCID 70066037HCID 70066037, compoundYield 80%

Procedure

To a solution of 5.70 g (17.0 mmol) of (2R)-(+)-2-hydroxymethyl-1-[4'-methoxyphenyl (2-tetrahydropyranyloxy)ethyl]pyrrolidine and 4.74 ml of triethylamine (40.0 mmol) in dichloromethane (100 ml) was added 2.37 ml (30.6 mmol) of methanesulfonylchloride and the mixture was stirred at room temperature for 16 hours. The mixture was diluted with dichloromethane and the solution was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silicagel column chromatography ((ethyl acetate)) to give 5.01 g (80%) of (3S)-(-)-3-chloro-[4-methoxyphenyl(2-tetrahydropyranyl)ethyl]piperidine as yellow oil.

Workup

  1. washthe solution was washed with water and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silicagel column chromatography ((ethyl acetate))

Sources & evidence

ORD record
ord-e6702857409b411295b37a4a9f5c626a
Source dataset
uspto-grants-2000_10
Patent number
US06127361

Reaction notes

Loading…