1-Propanol → HCID 53719935, compound

HRID 1590188Notes

Reaction equation

HRID 1590188 reaction equation
[CH2:1]([CH:8]([CH2:12][C:13]([N:15]1[CH2:23][C@H:22]2[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16]1)=[O:14])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](O)[CH2:25][CH3:26]>>[CH2:1]([CH:8]([CH2:12][C:13]([N:15]1[CH2:16][C@H:17]2[C@H:22]([CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:23]1)=[O:14])[C:9]([O:11][CH2:24][CH2:25][CH3:26])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10311-PropanolHCID 107341222-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid

Product 1

HCID 53719935HCID 53719935, compound

Procedure

To 2-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionic acid (100 mg) were added propanol (2 ml) and boron trifluoride diethyl ether complex (12 μl) with stirring. After the mixture was stirred at room temperature for 24 hours, the solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed succecively with saturated sodium bicarbonate solution and brine, and dried over MgSO4. The solvent was evaporated under reduced pressure to give 106 mg of propyl 2-benzyl-3-(cis-hexahydro-2-isoindolinylcarbonyl)propionate as a colorless viscous oil.

Workup

  1. stirringAfter the mixture was stirred at room temperature for 24 hours
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed succecively with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f4a4d8ab4581444bbec049a466e602c6
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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