(-)-Mandelic acid → (S)-(-)-1-Benzyl-3-pyrrolidinol

HRID 2211235Notes

Reaction equation

HRID 2211235 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:12]([N:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[C:1]([O-:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH2:12]([N:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 11914(-)-Mandelic acidHCID 69889N-benzyl-3-pyrrolidinol

Product 2

HCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinolHCID 3839223Mandelate ion

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 66 ml of acetone were dissolved 17.7 g of dl-1-benzyl-3-hydroxypyrrolidine and 15.2 g of D-(-)-mandelic acid with heating and the solution was allowed to stand overnight at 4° C. to deposit crystals. Then, 8.5 g of the crystals thus deposited were collected and recrystallized from 26 ml of acetone to provide 5.1 g of D-(-) -mandelate of (S)-(-)-1-benzyl-3-hydroxypyrrolidine. The specific rotation [α]D20 was -45.5° C. (c=1, methanol). When the recrystallization was further repeated, the specific rotation was not changed. The melting point was 101°-102° C.

Workup

  1. temperaturewith heating
  2. customThen, 8.5 g of the crystals thus deposited were collected
  3. customrecrystallized from 26 ml of acetone

Sources & evidence

ORD record
ord-fe052b7ce7cb4afd925f7be798fadb3f
Source dataset
uspto-grants-1995_10
Patent number
US05463064

Reaction notes

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