Sodium Carbonate → 2-Benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline

HRID 1494851Notes

Reaction equation

HRID 1494851 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Cl[C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>C(Cl)(Cl)Cl>[CH2:36]([O:35][C:33]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9]1)=[O:34])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 19828499N-BOC-(2-Benzylisoindolin-4-yl)methanamine

Product 1

HCID 198284932-Benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindolineYield 91.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3.38 g of 2-benzyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline was dissolved in 10 ml of chloroform and 1.27 g of sodium carbonate was added to it. To this solution was added dropwise 2.04 g of benzyl chloroformate under ice-cooling and stirring, and the mixture was stirred for 2 hours at room temperature. Insoluble materials were removed by filtration and the filtrate was concentrated. Recrystallization from ether gave 3.48 g of 2-benzyloxycarbonyl-4-(tertbutyloxycarbonylaminomethyl)isoindoline.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customInsoluble materials were removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customRecrystallization from ether

Sources & evidence

ORD record
ord-f8c0b66c1a854b0a89db90027aabecf8
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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