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

Base Information

Chemical Name:{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester
CAS No.:216006-00-7
Molecular Formula:C₂₂H₂₈N₂O₄
Molecular Weight:384.475
Hs Code.:

Synonyms:{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

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Chemical Property of {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

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Technology Process of {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

There total 23 articles about {2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic 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: 76.0%

: {2-[(R)-3-((E)-3,3-Diethoxy-propenyl)-1-(3,4-dimethoxy-phenyl)-4-oxo-cyclohex-2-enyl]-ethyl}-methyl-carbamic acid methyl ester

: 216006-00-7
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

Guidance literature:: With ammonium acetate; In acetic acid; at 100 ℃; for 24h;
DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

: 27124-93-2
1-(3,4-dimethoxyphenyl)cyclohexene

: 216006-00-7
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 18 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

13: 82 percent / various solvent(s) / 18 h / Heating

14: 73 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 2 h / -15 °C

15: 88 percent / I₂ / pyridine; CCl₄ / 20 h / Ambient temperature

16: 95 percent / i-Pr₂NH / PdCl₂(PPh₃)2, CuI / tetrahydrofuran / 0.67 h / 0 °C

17: 98 percent / H₂ / Lindlar catalyst / ethyl acetate / 3 h / Ambient temperature

18: 76 percent / NH₄OAc / acetic acid / 24 h / 100 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; 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; ammonium acetate; hydrogen; iodine; trimethylaluminum; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; potassium hexacyanoferrate(III); bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; copper(l) iodide; In tetrahydrofuran; pyridine; tetrachloromethane; diethyl ether; dichloromethane; water; acetic acid; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4039(98)01689-X

Reference yield:

: 216005-90-2
{2-[(1S,2R)-1-(3,4-Dimethoxy-phenyl)-2-hydroxy-cyclohexyl]-ethyl}-methyl-carbamic acid methyl ester

: 216006-00-7
{2-[(S)-6-(3,4-Dimethoxy-phenyl)-5,6,7,8-tetrahydro-quinolin-6-yl]-ethyl}-methyl-carbamic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / NaH / tetrahydrofuran / 6 h / Ambient temperature

2: 82 percent / various solvent(s) / 18 h / Heating

3: 73 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 2 h / -15 °C

4: 88 percent / I₂ / pyridine; CCl₄ / 20 h / Ambient temperature

5: 95 percent / i-Pr₂NH / PdCl₂(PPh₃)2, CuI / tetrahydrofuran / 0.67 h / 0 °C

6: 98 percent / H₂ / Lindlar catalyst / ethyl acetate / 3 h / Ambient temperature

7: 76 percent / NH₄OAc / acetic acid / 24 h / 100 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; ammonium acetate; hydrogen; iodine; sodium hydride; diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst; copper(l) iodide; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane; acetic acid; ethyl acetate;
DOI:10.1016/S0040-4039(98)01689-X