(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

Base Information

Chemical Name:(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester
CAS No.:160964-23-8
Molecular Formula:C₂₁H₂₂O₃
Molecular Weight:322.404
Hs Code.:

Synonyms:(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

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Chemical Property of (S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

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Technology Process of (S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

There total 13 articles about (S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester 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: 38.0%

: 26164-26-1
(S)-2-methoxy-2-phenylacetic acid

: (1aR,4S,8bR)-1,1a,2,3,4,8b-Hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-ol

: (S)-Methoxy-phenyl-acetic acid (1aR,4S,8bR)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

: 160964-23-8
(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 0.25h; Yields of byproduct given;
DOI:10.1021/jo00101a025

Reference yield:

: 52092-30-5
6,7-dihydro-5H-benzocyclohepten-5-one

: 160964-23-8
(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / 50percent aq. NaOH / TEBA / 15 h / 50 °C

2: 28 percent / benzene; hexane / 1 h / Irradiation

3: n-Bu₃SnH, AIBN / 3 h / 140 °C

4: Jones reagent

5: 76 percent / NaBH₄ / propan-2-ol / 3 h

6: 38 percent / DMAP, DCC / CH₂Cl₂ / 0.25 h

With dmap; sodium hydroxide; sodium tetrahydroborate; jones reagent; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; dicyclohexyl-carbodiimide; N-benzyl-N,N,N-triethylammonium chloride; In hexane; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1021/jo00101a025

Reference yield:

: 72472-29-8
9-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one

: 160964-23-8
(S)-Methoxy-phenyl-acetic acid (1aS,4R,8bS)-(1,1a,2,3,4,8b-hexahydro-benzo[a]cyclopropa[c]cyclohepten-4-yl) ester

Guidance literature:: Multi-step reaction with 7 steps

1: DBU

2: 75 percent / 50percent aq. NaOH / TEBA / 15 h / 50 °C

3: 28 percent / benzene; hexane / 1 h / Irradiation

4: n-Bu₃SnH, AIBN / 3 h / 140 °C

5: Jones reagent

6: 76 percent / NaBH₄ / propan-2-ol / 3 h

7: 38 percent / DMAP, DCC / CH₂Cl₂ / 0.25 h

With dmap; sodium hydroxide; sodium tetrahydroborate; jones reagent; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; N-benzyl-N,N,N-triethylammonium chloride; In hexane; dichloromethane; isopropyl alcohol; benzene;
DOI:10.1021/jo00101a025