4-Methylmorpholine → HCID 54553080, compound

HRID 1590179Notes

Reaction equation

HRID 1590179 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:38]1[C@@H:46]2[C@@H:41]([CH2:42][CH2:43][CH2:44][CH2:45]2)[CH2:40][NH:39]1>O1CCCC1>[CH2:16]([C@@H:11]([CH2:12][C:13]([N:39]1[CH2:40][C@H:41]2[C@H:46]([CH2:45][CH2:44][CH2:43][CH2:42]2)[CH2:38]1)=[O:15])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 10964494cis-OctahydroisoindoleHCID 14213079HCID 14213079, compound

Product 1

HCID 54553080HCID 54553080, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of (S)-3-benzyloxycarbonyl-4-phenylbutyric acid (671 mg) in anhydrous tetrahydrofuran (15 ml) were added N-methylmorpholine (0.5 ml) and isobutyl chloroformate (0.38 ml) with stirring at -20° C. for 20 minutes. To the mixture was added a solution of cis-hexahydroisoindoline (313 mg) in anhydrous tetrahydrofuran (5 ml) with stirring at -10 - -20° C. After 1 hour, the deposit was filtered off and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with 0.5N hydrochloric acid, saturated sodium bicarbonate solution, and brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was recrystallized from dichloromethane-hexane to give 772 mg of benzyl (S)-2-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionate.

Workup

  1. stirringwith stirring at -10 - -20° C
  2. waitAfter 1 hour
  3. filtrationthe deposit was filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with 0.5N hydrochloric acid, saturated sodium bicarbonate solution, and brine
  7. dry with materialdried over MgSO4
  8. customAfter the solvent was evaporated under reduced pressure
  9. customthe residue was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-c098edb3a3dd4d3a987b932c71c17bb2
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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