(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

Base Information

Chemical Name:(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one
CAS No.:1208110-26-2
Molecular Formula:C₂₃H₂₇NO₂
Molecular Weight:349.473
Hs Code.:

Synonyms:(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

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Chemical Property of (2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

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Technology Process of (2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

There total 14 articles about (2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one 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: 86.0%

: 1208109-86-7
6-methoxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride

: 1208110-26-2
(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

Guidance literature:: With hydrogen bromide; for 36h; Reflux;
DOI:10.1016/j.bmc.2017.05.012

Reference yield:

: 78348-46-6
N-benzoyl-2-piperidinecarboxylic acid

: 1208110-26-2
(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.5 h / -20 - -15 °C

1.2: 3 h / 20 °C

2.1: trichlorophosphate; pyridine / tetrahydrofuran; N,N-dimethyl-formamide / 27 h / 0 - 80 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 3.25 h / -78 - 20 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / 18 h / 20 °C

4.2: 48 h / 130 °C

5.1: sodium hydride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

5.2: 9 h / 120 °C

5.3: Cooling with ice

6.1: hydrogen bromide / 36 h / Reflux

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; chloroformic acid ethyl ester; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2017.05.012

Reference yield:

: 71413-04-2
(2RS)-1-benzoylpiperidine-2-carbonitrile

: 1208110-26-2
(2RS)-6-hydroxy-1'-[2-(2-methylphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 3.25 h / -78 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / toluene / 4 h / 20 °C

2.2: 18 h / 120 °C

3.1: sodium hydride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C

3.2: 9 h / 120 °C

3.3: Cooling with ice

4.1: hydrogen bromide / 36 h / Reflux

With hydrogen bromide; sodium hydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2017.05.012