Ammonium Hydroxide → HCID 22853592, compound

HRID 37037Notes

Reaction equation

HRID 37037 reaction equation
[CH2:1]([C@@H:4]([N:14]=[C:15]=[O:16])[C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:12][O:13][C:7]=2[CH:6]=1)[CH:2]=[CH2:3].[OH-].[NH4+:18]>C1COCC1>[CH2:1]([C@@H:4]([NH:14][C:15]([NH2:18])=[O:16])[C:5]1[CH:10]=[CH:9][C:8]2[O:11][CH2:12][O:13][C:7]=2[CH:6]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 18655100(R)-alpha-Allyl-(3,4-methylenedioxy)benzyl isocyanate

Product 1

HCID 22853592HCID 22853592, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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).

Workup

  1. customwas then evaporated to dryness in vacuo
  2. customchromatographed

Sources & evidence

ORD record
ord-3189451888394b7fbc42f36fa76435f2
Source dataset
uspto-grants-1995_05
Patent number
US05420010

Reaction notes

Loading…