(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Base Information

Chemical Name:(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate
CAS No.:157459-18-2
Molecular Formula:C₂₈H₂₉NO₄
Molecular Weight:443.543
Hs Code.:

Synonyms:(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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Chemical Property of (S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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Technology Process of (S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

There total 12 articles about (S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 38197-43-2
2-bromo-3-methylanisole

: 157459-18-2
(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: bromine / CCl₄ / 3 h / 0 °C

2: dimethyl sulfoxide / 1 h / Ambient temperature

3: BH₃*THF / tetrahydrofuran / 1 h / Heating

4: triethylamine / methanol / 0.5 h / Ambient temperature

5: n-butyllithium / hexane; diethyl ether / 1 h / -78 °C

6: pyridine, chromium (III) oxide, celite / CH₂Cl₂ / 1 h / Ambient temperature

7: potassium carbonate / methanol; H₂O / 4 h / Ambient temperature

8: sodium cyanoborohydride / methanol / 1 h / 0 °C

9: 37percent hydrochloric acid / methanol; H₂O / 12 h / Ambient temperature

10: 1M sodium hydroxide / CH₂Cl₂ / 1 h / Ambient temperature

11: toluene / 2 h / Heating

12: trimethyl phosphite / 26 h / Heating

With pyridine; hydrogenchloride; chromium(III) oxide; sodium hydroxide; n-butyllithium; borane-THF; Celite; bromine; sodium cyanoborohydride; potassium carbonate; dimethyl sulfoxide; triethylamine; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(01)80641-4

Reference yield:

: 121587-40-4
N-trifluoroacetyl-2-(2-bromo-3-methoxyphenyl)ethylamine

: 157459-18-2
(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: n-butyllithium / hexane; diethyl ether / 1 h / -78 °C

2: pyridine, chromium (III) oxide, celite / CH₂Cl₂ / 1 h / Ambient temperature

3: potassium carbonate / methanol; H₂O / 4 h / Ambient temperature

4: sodium cyanoborohydride / methanol / 1 h / 0 °C

5: 37percent hydrochloric acid / methanol; H₂O / 12 h / Ambient temperature

6: 1M sodium hydroxide / CH₂Cl₂ / 1 h / Ambient temperature

7: toluene / 2 h / Heating

8: trimethyl phosphite / 26 h / Heating

With pyridine; hydrogenchloride; chromium(III) oxide; sodium hydroxide; n-butyllithium; Celite; sodium cyanoborohydride; potassium carbonate; phosphorous acid trimethyl ester; In methanol; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(01)80641-4

Reference yield:

: 159411-84-4
(R)-1-<(1R,2R)-3-benzyloxy-1,2-dihydroxypropyl>-8-methoxy-1,2,3,4-tetrahydroisoquinoline

: 157459-18-2
(S)-benzyl 1-<(E)-3-benzyloxy-1-propenyl>-8-methoxy-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 1M sodium hydroxide / CH₂Cl₂ / 1 h / Ambient temperature

2: toluene / 2 h / Heating

3: trimethyl phosphite / 26 h / Heating

With sodium hydroxide; phosphorous acid trimethyl ester; In dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)80641-4