Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester
• CAS No.: 216005-91-3
• Molecular Formula: C₂₁H₃₁NO₅S₂
• Molecular Weight: 441.613

Synonyms:Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester

Chemical Property of Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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MSDS Files:

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Technology Process of Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester

There total 17 articles about Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-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: 91.0%

carbon disulfide (75-15-0,12122-00-8) + {2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2-hydroxy-cyclohexyl]-ethyl}-methyl-carbamic acid methyl ester (216005-90-2) + methyl iodide (74-88-4) → Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester (216005-91-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

1-(3,4-dimethoxyphenyl)cyclohexene (27124-93-2) → Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester (216005-91-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / AD-mix-α, K2CO3, K3Fe(CN)6, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / Ambient temperature

2: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

3: 98 percent / Et₃NSO₂NCO₂Me / toluene / 1 h / 50 °C

4: 98 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: 98 percent / NBS / diethyl ether / 24 h / 0 °C / to RT

6: 87 percent / Bu₃SnCl, AIBN, NaBH₄ / 2-methyl-propan-2-ol / 6 h / Heating

7: 93 percent / mCPBA, BF₃*OEt₂ / CH₂Cl₂ / 1 h / Ambient temperature

8: 98 percent / Me₃Al / tetrahydrofuran / 8 h / Heating

9: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C

10: LiAlH₄ / tetrahydrofuran / 48 h / Heating

11: Et₃N / CH₂Cl₂ / Ambient temperature

12: 91 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

With dmap; sodium tetrahydroborate; AD-mix-α; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; Burgess Reagent; 2,2'-azobis(isobutyronitrile); methanesulfonamide; boron trifluoride diethyl etherate; tributyltin chloride; trimethylaluminum; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol (189363-85-7) → Dithiocarbonic acid O-{(1R,2S)-2-(3,4-dimethoxy-phenyl)-2-[2-(methoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl} ester S-methyl ester (216005-91-3)

Guidance literature:

Multi-step reaction with 9 steps

2: 98 percent / NBS / diethyl ether / 24 h / 0 °C / to RT

3: 87 percent / Bu₃SnCl, AIBN, NaBH₄ / 2-methyl-propan-2-ol / 6 h / Heating

4: 93 percent / mCPBA, BF₃*OEt₂ / CH₂Cl₂ / 1 h / Ambient temperature

5: 98 percent / Me₃Al / tetrahydrofuran / 8 h / Heating

6: 1.) DMSO, (COCl)2; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C

7: LiAlH₄ / tetrahydrofuran / 48 h / Heating

8: Et₃N / CH₂Cl₂ / Ambient temperature

9: 91 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

With sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tributyltin chloride; trimethylaluminum; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01689-X

upstream raw materials:

carbon disulfide

{2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2-hydroxy-cyclohexyl]-ethyl}-methyl-carbamic acid methyl ester

methyl iodide

1-(3,4-dimethoxyphenyl)cyclohexene

Downstream raw materials:

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

(-)-mesembrine

{2-[(R)-1-(3,4-Dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-amine

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