Reaction #60396

Reaction equation

(7-cyano-chroman-4-yl)-carbamic acid tert-butyl ester

NaH

Iodomethane

→

title compound

(7-cyano-chroman-4-yl)-methyl-carbamic acid tert-butyl ester

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting mixture was stirred at RT for 21 h
2. 2
   OtherThe reaction was quenched with saturated NH4Cl (40 mL) DMF
3. 3
   Otherwas removed with a rotary evaporator at 70° C
4. 4
   workup.ADDITIONThe crude was diluted with H2O (100 mL)
5. 5
   Extractionextracted with EtOAc (80 mL×4)
6. 6
   WashThe extract phase was washed with saturated NaCl
7. 7
   Dryingdried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated

Procedure

A mixture of (7-cyano-chroman-4-yl)-carbamic acid tert-butyl ester (769 mg, 2.81 mmol, 1.0 eq), NaH (Aldrich, 449 mg (60% by weight), 11.2 mmol, 4.0 eq) in DMF (15 mL) was stirred at RT for 3 h. Iodomethane (Aldrich, 1.99 g, 14.1 mmol, 5.0 eq) was added slowly. The resulting mixture was stirred at RT for 21 h. The reaction was quenched with saturated NH4Cl (40 mL) DMF was removed with a rotary evaporator at 70° C. The crude was diluted with H2O (100 mL), extracted with EtOAc (80 mL×4). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-15% EtOAc-Hexane) afforded the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 289 (M+1).

Source