(1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester
• CAS No.: 110174-18-0
• Molecular Formula: C₂₅H₂₇F₃O₇
• Molecular Weight: 496.48

Synonyms:(1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property of (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester

There total 42 articles about (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl 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:

1-iodo-5-methoxynaphthalene (61735-51-1) → (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester (110174-18-0)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 8 min, 2.) THF, -78 deg C

2: oxalyl chloride / CH₂Cl₂ / 12 h / Ambient temperature

3: conc. ammonia / CHCl₃

4: 1.) triethyloxonium tetrafluoroborate / 1.) CH₂Cl₂, a) RT, 20 h, b) reflux, 5 h, 2.) CH₂Cl₂, reflux, 24 h

5: 2.) a) CF₃COOH, b) H₂O / 1.) THF, Et₂O, -60 deg C, 72 h, 2.) a) -78 deg C, 1 h

6: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

7: 89.9 percent / KOH, benzyltriethylammonium chloride / CH₂Cl₂ / 20 h / Ambient temperature

8: 81.2 percent / O₂, PdCl₂(MeCN)2, CuCl / methanol / 20 h / 45 °C

9: 1.) sodium hexamethyldisilazane, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 40 min

10: 97.2 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2068.6 Torr / Ambient temperature

11: 97.1 percent / NaBH₄ / methanol / 1.5 h

12: Et₃N / CH₂Cl₂ / 1 h / 0 °C

13: LiAlH₄ / diethyl ether / 2 h / Heating

14: 98.3 percent / H₂ / 10percent Pd/C / methanol / 8 h / 2068.6 Torr / Ambient temperature

15: NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

16: Jones reagent / acetone / 3 h / 0 °C

17: 99 percent / diethyl ether / 1 h / 0 °C

18: 1.) N-bromosuccinimide, 2.) H₂O / 1.) CCl₄, 10 deg C, 30 min, irrad., 2.) THF, 25 deg C, 2 h

19: Et₃N, DMAP / 0.5 h / Ambient temperature

With dmap; ruthenium trichloride; dichloro bis(acetonitrile) palladium(II); potassium hydroxide; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; jones reagent; oxalyl dichloride; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; oxygen; triethyloxonium fluoroborate; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00229a028

Reference yield:

1-iodo-5-methoxynaphthalene (61735-51-1) → (1R,2R,4S)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester (110174-18-0)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 8 min, 2.) THF, -78 deg C

2: oxalyl chloride / CH₂Cl₂ / 12 h / Ambient temperature

3: conc. ammonia / CHCl₃

4: 1.) triethyloxonium tetrafluoroborate / 1.) CH₂Cl₂, a) RT, 20 h, b) reflux, 5 h, 2.) CH₂Cl₂, reflux, 24 h

5: 2.) a) CF₃COOH, b) H₂O / 1.) THF, Et₂O, -60 deg C, 72 h, 2.) a) -78 deg C, 1 h

6: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

7: 89.9 percent / KOH, benzyltriethylammonium chloride / CH₂Cl₂ / 20 h / Ambient temperature

8: 81.2 percent / O₂, PdCl₂(MeCN)2, CuCl / methanol / 20 h / 45 °C

9: 1.) sodium hexamethyldisilazane, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 40 min

10: 97.2 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2068.6 Torr / Ambient temperature

11: 97.1 percent / NaBH₄ / methanol / 1.5 h

12: Et₃N / CH₂Cl₂ / 1 h / 0 °C

13: LiAlH₄ / diethyl ether / 2 h / Heating

14: 98.3 percent / H₂ / 10percent Pd/C / methanol / 8 h / 2068.6 Torr / Ambient temperature

15: NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

16: Jones reagent / acetone / 3 h / 0 °C

17: 99 percent / diethyl ether / 1 h / 0 °C

18: 1.) N-bromosuccinimide, 2.) H₂O / 1.) CCl₄, 10 deg C, 30 min, irrad., 2.) THF, 25 deg C, 2 h

19: Et₃N, DMAP / 0.5 h / Ambient temperature

With dmap; ruthenium trichloride; dichloro bis(acetonitrile) palladium(II); potassium hydroxide; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; jones reagent; oxalyl dichloride; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; oxygen; triethyloxonium fluoroborate; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00229a028

Reference yield:

5-methoxy-1-naphthoic acid (51934-37-3) → (1S,2S,4R)-2-Ethyl-2-hydroxy-5-methoxy-4-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid methyl ester (110174-18-0)

Guidance literature:

Multi-step reaction with 18 steps

1: oxalyl chloride / CH₂Cl₂ / 12 h / Ambient temperature

2: conc. ammonia / CHCl₃

3: 1.) triethyloxonium tetrafluoroborate / 1.) CH₂Cl₂, a) RT, 20 h, b) reflux, 5 h, 2.) CH₂Cl₂, reflux, 24 h

4: 2.) a) CF₃COOH, b) H₂O / 1.) THF, Et₂O, -60 deg C, 72 h, 2.) a) -78 deg C, 1 h

5: LiAlH₄ / diethyl ether / 1 h / Ambient temperature

6: 89.9 percent / KOH, benzyltriethylammonium chloride / CH₂Cl₂ / 20 h / Ambient temperature

7: 81.2 percent / O₂, PdCl₂(MeCN)2, CuCl / methanol / 20 h / 45 °C

8: 1.) sodium hexamethyldisilazane, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 40 min

9: 97.2 percent / H₂ / 10percent Pd/C / methanol / 4 h / 2068.6 Torr / Ambient temperature

10: 97.1 percent / NaBH₄ / methanol / 1.5 h

11: Et₃N / CH₂Cl₂ / 1 h / 0 °C

12: LiAlH₄ / diethyl ether / 2 h / Heating

13: 98.3 percent / H₂ / 10percent Pd/C / methanol / 8 h / 2068.6 Torr / Ambient temperature

14: NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

15: Jones reagent / acetone / 3 h / 0 °C

16: 99 percent / diethyl ether / 1 h / 0 °C

17: 1.) N-bromosuccinimide, 2.) H₂O / 1.) CCl₄, 10 deg C, 30 min, irrad., 2.) THF, 25 deg C, 2 h

18: Et₃N, DMAP / 0.5 h / Ambient temperature

With dmap; ruthenium trichloride; dichloro bis(acetonitrile) palladium(II); potassium hydroxide; ammonium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; oxalyl dichloride; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen; oxygen; triethyloxonium fluoroborate; sodium hexamethyldisilazane; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; trifluoroacetic acid; copper(l) chloride; palladium on activated charcoal; In methanol; tetrachloromethane; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00229a028

upstream raw materials:

(R)-methoxytrifluoromethylphenylacetyl chloride

1-carbomethoxy-2-ethyl-2,4-dihydroxy-5-methyl-1,2,3,4-tetrahydronaphthalene

1-iodo-5-methoxynaphthalene

5-methoxy-1-naphthoic acid

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