Methyl chloroformate → Methyl 2,3-dihydro-1H-indole-1-carboxylate

A mixture of indoline (11.97 g, 0.1 mol), methyl chloroformate (15.45 mL, 0.2 mol), triethylamine (40.4 g, 0.4 mol), and DMAP (0.5 g, 0.004 mol) in CH2Cl2 (100 mL) was stirred for 16 hours. The reaction mixture was quenched with water (10 mL). The reaction was extracted with CH2Cl2 (1×40 mL). The organic layer washed with water (1×50 mL), dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated in vacuo to provide the title compound (17.6 g, 99%) which was used without further purification.

1. customThe reaction mixture was quenched with water (10 mL)
2. extractionThe reaction was extracted with CH2Cl2 (1×40 mL)
3. washThe organic layer washed with water (1×50 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationthe resultant filtrate was concentrated in vacuo

ORD record

ord-fb6e172a4c7c470882b10a1552740b38

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06831080B2