Methylenetriphenylphosphorane → HCID 23467857, compound

HRID 1389140Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[CH2:14][CH2:13][C:12]34[C:15]5[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:16]=5[O:17][CH:11]3[C:10](=O)[CH2:9][CH2:8][CH:7]4[CH2:6]2)[CH2:3][CH2:2]1.[CH2:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH:1]1([CH2:4][N:5]2[CH2:14][CH2:13][C:12]34[C:15]5[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:16]=5[O:17][CH:11]3[CH:10]([CH3:25])[CH2:9][CH2:8][CH:7]4[CH2:6]2)[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 137960Methylenetriphenylphosphorane

HCID 23467874HCID 23467874, compound

Product 1

HCID 23467857HCID 23467857, compound

Procedure

Oxidation of XI ##STR98## with chromium trioxide gives 3-cyclopropylmethyl-9-methoxy-2,4,4a,5,6,7-hexahydro-1H-benzo[4,5]furo[3,2-e]isoquinolin-7[3H]-one ##STR99## Reaction of this compound with methylenetriphenylphosphorane followed by catalytic hydrogenation of the resulting 7-methylene derivative gives 3-cyclopropylmethyl-9-methoxy-7-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline ##STR100##

Sources & evidence

ORD record: ord-4825e53e98d64847aad780f521d922b4
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243668

Reaction notes

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