(S)-mandelic acid → HCID 15838546, compound

HRID 742015Notes

Reaction equation

HRID 742015 reaction equation
[NH2:1][C:2]1[C:24]([CH3:25])=[C:23]([CH3:26])[C:5]2[O:6][C:7]([CH3:22])([CH2:9][N:10]3[CH2:15][CH2:14][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][CH2:11]3)[CH2:8][C:4]=2[C:3]=1[CH3:27].[C:28]([OH:38])(=[O:37])[C@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[OH:30]>C(Cl)(Cl)Cl.CO>[C:28]([OH:38])(=[O:37])[C@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[OH:30].[NH2:1][C:2]1[C:24]([CH3:25])=[C:23]([CH3:26])[C:5]2[O:6][C@:7]([CH3:22])([CH2:9][N:10]3[CH2:15][CH2:14][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][CH2:11]3)[CH2:8][C:4]=2[C:3]=1[CH3:27]

Participants

5

Reactant 2

HCID 439616(S)-mandelic acidHCID 9863888HCID 9863888, compound

Product 1

HCID 15838546HCID 15838546, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 35.4 g of (±)-5-amino-2,4,6,7-tetramethyl-2-(4-phenylpiperidinomethyl)-2,3-dihydrobenzo[b]furan in 500 ml of chloroform was added a solution of 14.78 g of (S)--(+)--mandelic acid in 300 ml of methanol, followed by concentration. To the residue was added about 500 ml of ether; the resulting precipitate was collected by filtration and washed with ether. The resulting 35.4 g crude crystal was subjected to the following recrystallizing procedure. Specifically, the crude crystal was dissolved in methanol-acetonitrile (2:1) (1 liter). After the solution was concentrated to about 100 ml volume, about 500 ml of ether was added, and the mixture was kept standing at 20° C. The resulting precipitate was finely milled, then filtered and washed witch ether. The above procedure was repeated in two cycles (first yield 21.96 g) to yield 19.90 g of (S)--(+)-5-amino-2,4,6,7-tetramethyl-2-(4-phenylpiperidinomethyl)-2,3-dihydrobenzo[b]furan (S)--(+)--mandelate.

Workup

  1. concentrationfollowed by concentration
  2. additionTo the residue was added about 500 ml of ether
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with ether
  5. customfollowing recrystallizing procedure
  6. dissolutionSpecifically, the crude crystal was dissolved in methanol-acetonitrile (2:1) (1 liter)
  7. concentrationAfter the solution was concentrated to about 100 ml volume, about 500 ml of ether
  8. additionwas added
  9. customwas kept standing at 20° C
  10. customThe resulting precipitate was finely milled
  11. filtrationfiltered
  12. washwashed witch ether

Sources & evidence

ORD record
ord-b20b1f82c93b4a6aa68d3dce6843f523
Source dataset
uspto-grants-1996_09
Patent number
US05552552

Reaction notes

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