1-Phenethylamine → HCID 86750893, compound

HRID 1781548Notes

Reaction equation

HRID 1781548 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[C:9]([O:21][CH3:22])[C:8]([CH3:23])=[C:7]2[C:3]=1[C:4](=[O:24])[O:5][CH2:6]2.[CH3:25][CH:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O>[CH3:25][CH:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH:1][C:2]1[C:10]([CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[C:9]([O:21][CH3:22])[C:8]([CH3:23])=[C:7]2[C:3]=1[C:4](=[O:24])[O:5][CH2:6]2

Participants

4

Reactant 2

HCID 74081-PhenethylamineHCID 54488078HCID 54488078, compound

Product 1

HCID 86750893HCID 86750893, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of the 85:13 acid mixture(E) 6-(1,3-dihydro-4-hydroxy -6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoic acid (810 g, 2.4 mol,) was dissolved in acetone (16L) at 40° C. and (+)-α-methylbenzylamine (800 g, 6.6 mol) was added. Upon cooling, the salt crystallized and was collected by filtration. Recrystallization from acetone (8L) containing (+)-α-methylbenzylamine (202 g) afforded (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -2,4-dimethyl-4-hexenoic acid (+)α-Methylbenzylamine salt after drying as off-white needles, m.p. 147°-9° C.

Workup

  1. temperatureUpon cooling
  2. customthe salt crystallized
  3. filtrationwas collected by filtration
  4. customRecrystallization from acetone (8L)
  5. additioncontaining (+)-α-methylbenzylamine (202 g)

Sources & evidence

ORD record
ord-3c98506f7b5947428a6899a4897143df
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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