Reaction #1622

ord-265f1fbbd21744dfa0e52587c35414e9

Reaction equation

CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1.Cl
(R)-5-(2-aminopropyl)-1,3-benzodioxole-2,2-dicarboxylic acid diethyl ester hydrochloride
O=C([O-])O.[Na+]
sodium hydrogen carbonate
CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1
title compound
CCOC(=O)C1(C(=O)OCC)Oc2ccc(C[C@@H](C)N)cc2O1
(R)-5-(2-Aminopropyl)-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe organic layer was separated
  2. 2
    Extractionthe aqueous layer was extracted with dichloromethane (2×50 ml)
  3. 3
    WashThe combined organic extracts were washed with water (50 ml) and brine (50 ml)
  4. 4
    Dryingdried (MgSO4)
  5. 5
    OtherThe solvent was evaporated

Procedure

A solution of (R)-5-(2-aminopropyl)-1,3-benzodioxole-2,2-dicarboxylic acid diethyl ester hydrochloride (646 mg, 2 mMol) in dichloromethane (80 ml) was shaken with a saturated solution of sodium hydrogen carbonate (20 ml) for 30 seconds. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 ml). The combined organic extracts were washed with water (50 ml) and brine (50 ml), dried (MgSO4). The solvent was evaporated giving the title compound which was used immediately.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726165uspto-grants-1998_03