Di-tert-butyl dicarbonate → HCID 67718683, compound

HRID 1780973Notes

Reaction equation

HRID 1780973 reaction equation
Cl.[C:2]([O:5][CH:6]1[CH2:14][C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]2[CH:8]([CH2:9][NH:10][CH2:11]2)[C:7]1=[O:27])(=[O:4])[CH3:3].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>ClCCl.CN(C)C1C=CN=CC=1>[C:2]([O:5][CH:6]1[CH2:14][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]2[CH:8]([CH2:9][NH:10][CH2:11]2)[C:7]1=[O:27])(=[O:4])[CH3:3]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 67718682HCID 67718682, compound

Product 1

HCID 67718683HCID 67718683, compoundYield 122.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 19 g of (3aRS,5RS,7aRS)-5-acetoxy-7,7-diphenylperhydro-4-isoindolone hydrochloride in 200 cm3 of dry dichloromethane are added, at a temperature in the region of 5° C., with stirring, 46.9 cm3 of triethylemine and 11.8 g of di-tert-butyl dicarbonate, followed by 0.3 g of 4-dimethylaminopyridine. The reaction mixture is stirred at room temperature for 24 hours and then washed with saturated aqueous sodium bicarbonate solution. The organic phase is separated off after settling, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 120 cm3 of diisopropyl ether. 21 g of (3aRS,5RS,7aRS)-5-Acetoxy-7,7-diphenylperhydro-4-isoindolone are obtained, in the form of white crystals melting at 213° C.

Workup

  1. additionare added, at a temperature in the region of 5° C.
  2. stirringThe reaction mixture is stirred at room temperature for 24 hours
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. customThe organic phase is separated off
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customThe residue is crystallized in 120 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-72108bf20bb841af83b71a8c2b37018c
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

Loading…