Acetic Anhydride → 2-Pyrrolidineethanol, alpha-(3-methoxyphenyl)-1-methyl-, acetate (ester), (R*,S*)-

HRID 2049660Notes

Reaction equation

HRID 2049660 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]([OH:17])[CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[C:20](OC(=O)C)(=[O:22])[CH3:21]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]([O:17][C:20](=[O:22])[CH3:21])[CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 30543502-Pyrrolidineethanol, alpha-(3-methoxyphenyl)-1-methyl-, (R*,S*)-

Product 1

HCID 30543582-Pyrrolidineethanol, alpha-(3-methoxyphenyl)-1-methyl-, acetate (ester), (R*,S*)-

Procedure

3,5 g of (R*,S*)-1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)-ethanol and 40 ml of acetic acid anhydride are stirred for 15 minutes at room temperature. 6 N sodium hydroxide solution is added with cooling up to a pH of 8-9. The mixture is extracted with diethyl ether, and the organic layer is concentrated to the oily title compound. The hydrochloride (from methanol/diethyl ether) melts at 155°-157°.

Workup

  1. temperaturewith cooling up to a pH of 8-9
  2. extractionThe mixture is extracted with diethyl ether
  3. concentrationthe organic layer is concentrated to the oily title compound

Sources & evidence

ORD record
ord-0c2a1dc78aa24b82a0a9768b7b939603
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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