Methanol → HCID 19697682, compound

HRID 863284Notes

Reaction equation

HRID 863284 reaction equation
C(OC([N:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:13]([CH2:21][O:22][CH2:23][CH:24]=[CH2:25])[CH2:12]1)=O)C1C=CC=CC=1.CO>C(Cl)Cl>[CH2:23]([O:22][CH2:21][CH:13]1[CH2:12][NH:11][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14]1)[CH:24]=[CH2:25]

Participants

4

Reactant 2

HCID 887MethanolHCID 19697684HCID 19697684, compound

Product 1

HCID 19697682HCID 19697682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.8 ml of iododtrimethylsilane is added to a solution of 1.37 g of N-benzyloxycarbonyl-2(R,S)allyloxymethyl-3,4-dihydro-2H-1,4-benzoxazine in 25 ml of methylene chloride under argon. The reaction mixture is stirred at room temperature for 2 h, 10 ml of methanol are then added and the mixture is concentrated. The residue is extracted twice with 50 ml of a 10:1 mixture of hexane and diethyl ether and then dissolved in ethyl acetate, and the solution is washed with a 1N sodium carbonate solution and saturated sodium chloride solution. The crude product is purified by means of FC (100 g of silica gel, mobile phase D). This gives the pure title compound: Rf (D)=0.17.

Workup

  1. concentrationthe mixture is concentrated
  2. extractionThe residue is extracted twice with 50 ml of a 10:1 mixture of hexane and diethyl ether
  3. dissolutiondissolved in ethyl acetate
  4. washthe solution is washed with a 1N sodium carbonate solution and saturated sodium chloride solution
  5. customThe crude product is purified by means of FC (100 g of silica gel, mobile phase D)

Sources & evidence

ORD record
ord-c3fe49897de741b7a2244a88a5423490
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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