Allyl bromide → HCID 19697684, compound

HRID 863285Notes

Reaction equation

HRID 863285 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.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:34][CH:35]=[CH2:36].C(OC(N[C@@H](C[C@@H](C)CCO[Si](C(C)C)(C(C)C)C(C)C)C=O)=O)(C)(C)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[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][CH2:36][CH:35]=[CH2:34])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19697557HCID 19697557, compoundHCID 22882392HCID 22882392, compound

Product 1

HCID 19697684HCID 19697684, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound is prepared starting from 3.0 g of N-benzyloxycarbonyl-2(R,S)-hydroxymethyl-3,4-dihydro-2H-1,4-benzoxazine, 2.75 g of sodium bis(trimethylsilyl)amide and 1.7 ml of 3-bromo-1-propene analogously to Example 61): Rf (D)=0.32; Rf (3:1 mixture of toluene and ethyl acetate)=0.61.

Sources & evidence

ORD record
ord-2a02e691e296417a9ca23b3d95c27fe8
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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