Ethanol → HCID 9905364, compound

HRID 1719881Notes

Reaction equation

HRID 1719881 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C@H:16]1[CH2:20][CH2:19][C@H:18]([C:21](=[O:31])[C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[NH:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+].C(O)C>CO>[CH2:8]([CH:16]1[CH2:20][CH2:19][CH:18]([CH:21]([OH:31])[C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[NH:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 86740337HCID 86740337, compound

Product 1

HCID 9905364HCID 9905364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrolidine trifluoroacetate (XIV) is reduced with metal borohydride, preferably with sodium borohydride, in a lower alcohol, preferably ethanol or methanol, at -10° to +20° C. The solvent is removed, the aqueous residue is diluted with the solution of base, preferably saturated sodium carbonate, and the product is extracted to organic halogenated solvent, preferably dichloromethane, to result in ±trans erythro 2-[phenethyl]-5-[(3,4-methylenedioxy)-α-hydroxybenzyl]pyrrolidine compound (XV). ##STR16##

Workup

  1. customThe solvent is removed
  2. additionthe aqueous residue is diluted with the solution of base, preferably saturated sodium carbonate
  3. extractionthe product is extracted to organic halogenated solvent, preferably dichloromethane

Sources & evidence

ORD record
ord-9bd898fb93e34e8e8f45cdbfc1350a82
Source dataset
uspto-grants-1985_09
Patent number
US04543361

Reaction notes

Loading…