Reaction #65315

Reaction equation

(R)-α-allyl-(3,4-methylenedioxy)benzyl isocyanate

(R)-α-Allyl-(3,4-methylenedioxy)benzyl isocyanate

ammonium hydroxide

→

title compound

Yield 93.0%

N-[(R)-α-Allyl-(3,4-methylenedioxy)benzyl] urea

Yield 93.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherwas then evaporated to dryness in vacuo
2. 2
   Otherchromatographed

Procedure

To a solution of (R)-α-allyl-(3,4-methylenedioxy)benzyl isocyanate (6) (400 mg, 1.84 mmol) in THF (10 mL) was added 7.4 M ammonium hydroxide (0.75 mL, 5.5 mmol). The reaction was stirred at room temperature for 1 hour and was then evaporated to dryness in vacuo. The residue was flash chromatographed using 60%-100% ethyl acetate/hexanes to obtain 400 mg (93%) of the title compound as a white solid. NMR (CDCl3): δ 2.46 (t, J=7 Hz, 2 H), 3.8-4.8 (v b s, 2 H), 4.59 (v br q, J=7 Hz, 1 H), 5.0-5.2 (m, 3 H), 5.6-5.8 (m, 1 H), 5.95 (s, 2 H), 6.76 (s, 2 H), 6.79 (s, 1 H).

Source