(1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol

Base Information

• Chemical Name: (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol
• CAS No.: 73179-03-0
• Molecular Formula: C₂₅H₃₁NO₄Se
• Molecular Weight: 488.485

Synonyms:(1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol

Chemical Property of (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol

Chemical Property:

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Technology Process of (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol

There total 12 articles about (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol 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: 98.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + 3-Hydroxy-2-<2-(3-methoxybicyclo<4.2.0>octa-1,3,5-trien-7-yl)ethyl>-2-methylcyclopentaneethanol (73179-02-9) → (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol (73179-03-0)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo01299a042

Reference yield:

2-(4-Methoxybenzocyclobutenyl)ethyl iodide (60100-25-6) → (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol (73179-03-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / Lithium diisopropylamide / tetrahydrofuran / 1.) -78 to 0 deg C, 35 min, 2.) 0 deg C, 1.5 h

2: 84 percent / LiAlH₄ / tetrahydrofuran / 18 h / 60 °C

3: 100 percent / Pyridine / CH₂Cl₂ / 1.) 0 deg C, 2.) 5 deg C, 15 h, 3.) 25 deg C, 3 h

4: 95 percent / Lithium triethylborohydride / tetrahydrofuran / 3 h / 25 °C

5: 95 percent / aq. HCl / tetrahydrofuran / 5 h / Ambient temperature

6: aq. NaOH, aq. H₂O₂ / methanol; tetrahydrofuran; H₂O / 1.) 0 deg C, 2.) 34 h room temp.

7: diethyl ether

8: 84 percent / H₂ / PtO₂ / ethyl acetate / 1.5 h / Ambient temperature

9: 94 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

10: 98 percent / Tri-n-butylphosphine / tetrahydrofuran / 2 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo01299a042

Reference yield:

7-<2-(3-Methoxybicyclo<4.2.0>octa-1,3,5-trien-7-yl)ethyl>-7-methylbicyclo<2.2.1>hept-5-en-2-one (73178-94-6) → (1S,2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl)-ethyl]-2-methyl-3-[2-(2-nitro-phenylselanyl)-ethyl]-cyclopentanol (73179-03-0)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaOH, aq. H₂O₂ / methanol; tetrahydrofuran; H₂O / 1.) 0 deg C, 2.) 34 h room temp.

2: diethyl ether

3: 84 percent / H₂ / PtO₂ / ethyl acetate / 1.5 h / Ambient temperature

4: 94 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: 98 percent / Tri-n-butylphosphine / tetrahydrofuran / 2 h / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; tributylphosphine; hydrogen; dihydrogen peroxide; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate;

DOI:10.1021/jo01299a042

upstream raw materials:

ortho-nitrophenyl selenocyanate

3-Hydroxy-2-<2-(3-methoxybicyclo<4.2.0>octa-1,3,5-trien-7-yl)ethyl>-2-methylcyclopentaneethanol

2-(4-Methoxybenzocyclobutenyl)ethyl iodide

7-<2-(3-Methoxybicyclo<4.2.0>octa-1,3,5-trien-7-yl)ethyl>-7-methylbicyclo<2.2.1>hept-5-en-2-one

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