HCID 23467841, compound → HCID 23467839, compound

HRID 1389141Notes

Reaction equation

HRID 1389141 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][C:11]3=[CH:10][CH:9]=[CH:8][CH:7]4[C:6]2=[O:24])[CH2:3][CH2:2]1.[H][H]>>[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[CH2:10][CH2:9][CH:8]=[C:7]4[C:6]2=[O:24])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 23467841HCID 23467841, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23467839HCID 23467839, compound

Procedure

Catalytic hydrogenation of 3-cyclopropylmethyl 9-methoxy-2,3-dihydro-1H-benzo[4,5]furo[3,2-e]isoquinolin-4[4H]-one (Example 4c) is carried out as in Example 4d but the reaction is stopped after one mole equivalent of hydrogen has been taken up, giving 3-cyclopropylmethyl-9-methoxy-2,6,7,7a-tetrahydro-1H-benzo[4,5]furo[3,2-e]isoquinolin-4[3H]-one. This, on treatment with m-chloroperbenzoic acid gives 3-cyclopropylmethyl-4a,5-epoxy-9-methoxy-2,4a,5,6,7,7a-hexahydro-1H-benzo[4,5]furo[3,2-e]isoquinolin-4[3H]-one which is reduced with lithium aluminum hydride to 3-cyclopropylmethyl-9-methoxy-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinolin-4a-ol.

Sources & evidence

ORD record
ord-217a40b246294760b3a68e04fc17a9ab
Source dataset
uspto-grants-1981_01
Patent number
US04243668

Reaction notes

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