Allyl bromide → HCID 23467854, compound

HRID 1389139Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[O:9][CH:10]3[CH2:19][CH2:18][CH2:17][CH:16]4[C:11]3([CH2:12][CH2:13][NH:14][CH2:15]4)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:20](Br)[CH:21]=[CH2:22].C(=O)([O-])[O-].[K+].[K+]>>[CH2:22]([N:14]1[CH2:13][CH2:12][C:11]23[C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=4[O:9][CH:10]2[CH2:19][CH2:18][CH2:17][CH:16]3[CH2:15]1)[CH:21]=[CH2:20]

Participants

Reactant 3

HCID 7841Allyl bromide

HCID 11430Potassium Carbonate

HCID 23467856HCID 23467856, compound

Product 1

HCID 23467854HCID 23467854, compound

Procedure

Thus, 9-methoxy-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline, when treated with allyl bromide in the presence of a base such as potassium carbonate, gives 3-allyl-9-methoxy-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline (R1 =CH2CH=CH2 ; R2 =MeO; R3, R4, R5 =H). Also, thienyl or furyl carbonyl chlorides followed by reduction with lithium aluminum hydride give 3-(2-thienylmethyl or 2-furylmethyl-9-methoxy-2,3,4,4a,5,6,7,7a-octahydro-1H-benzo[4,5]furo[3,2-e]isoquinoline ##STR81##

Sources & evidence

ORD record: ord-1c217df89f6b4216aa0282f921a75422
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04243668

Reaction notes

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