Benzyl chloroformate → (5,6-Difluoro-1-oxoindan-2-yl)carbamic acid benzyl ester

HRID 2060884Notes

Reaction equation

HRID 2060884 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([F:12])=[C:7]([F:11])[CH:8]=2)[C:3]1=[O:13].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C([O-])(O)=O.[Na+]>[CH2:18]([O:17][C:15](=[O:16])[NH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([F:12])=[C:7]([F:11])[CH:8]=2)[C:3]1=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 575859182-Amino-5,6-difluoroindan-1-one

Product 1

HCID 59401382(5,6-Difluoro-1-oxoindan-2-yl)carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To 2-amino-5,6-difluoroindan-1-one (Preparation 78) (165 mg, 0.90 mmol) in saturated NaHCO3 (15 mL) was added benzyl chloroformate (0.15 mL, 1.08 mmol). The reaction mixture was stirred at rt for 1 h. The mixture was extracted with EtOAc (25 mL) and the organic phase washed with water (20 mL), brine (20 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (MeOH:DCM 1:99) to give the title compound: RT=3.50 min; m/z (ES+)=318.1 [M+H]+.

Workup

  1. extractionThe mixture was extracted with EtOAc (25 mL)
  2. washthe organic phase washed with water (20 mL), brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (MeOH:DCM 1:99)

Sources & evidence

ORD record
ord-92ba7b53551d4711a9fd272b627205b9
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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