Toluene → HCID 19697861, compound

HRID 863286Notes

Reaction equation

HRID 863286 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH:13]([CH2:21][OH:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([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][CH3:23])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19697557HCID 19697557, compound

Product 1

HCID 19697861HCID 19697861, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound is prepared analogously to Example 87b) starting from 3.0 g of N-benzyloxycarbonyl-2(R,S)-hydroxymethyl-3,4-dihydro-2H-1,4-benzoxazine, 2.4 g of sodium bis(trimethylsilyl)amide and 0.94 ml of methyliodide: Rf (3:1 mixture of toluene and ethyl acetate)=0.56; Rt (I)=27.9 min.

Sources & evidence

ORD record
ord-f5c788d3ee744dceb834d34e59bfc03e
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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