4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

Base Information

Chemical Name:4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile
CAS No.:150461-19-1
Molecular Formula:C₂₅H₂₇ClN₂OS
Molecular Weight:439.021
Hs Code.:

Synonyms:4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

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Chemical Property of 4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

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Technology Process of 4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

There total 9 articles about 4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile 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: 99.0%

: 150461-54-4
4-<1-(4-chlorobenzyl)-4-methyl-6-carbomethoxy-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

: 150461-19-1
4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

Guidance literature:: With lithium borohydride; In tetrahydrofuran; for 16h; Ambient temperature;
DOI:10.1021/jm00071a008

Reference yield:

: 144396-98-5
methyl 3-<1-(4-chlorobenzyl)-3-(tert-butylthio)-5-(allyloxy)indol-2-yl>-2,2-dimethylpropanoate

: 150461-19-1
4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

3: dimethylformamide; dimethylsulfoxide / 1 h / 125 °C

4: 2.) p-toluenesulfonic acid / 1.) 1,2-dichlorobenzene, reflux, 16 h, 2.) 1,2-dichlorobenzene, 150 deg C, 45 min

5: 79 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

6: 88 percent / Et₃N, (diphenylphosphino)ethane, Pd(OAc)2 / dimethylsulfoxide; methanol / 48 h / 70 - 80 °C

7: 99 percent / LiBH₄ / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; palladium diacetate; lithium aluminium tetrahydride; lithium borohydride; toluene-4-sulfonic acid; triethylamine; ethyl-diphenyl-phosphane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm00071a008

Reference yield:

: methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate

: 150461-19-1
4-<1-(4-chlorobenzyl)-4-methyl-6-(hydroxymethyl)-4,5-dihydro-1H-thiopyrano<2,3,4-c,d>indol-2-yl>-3,3-dimethylbutyronitrile

Guidance literature:: Multi-step reaction with 8 steps

1: 31 percent / NaOAc, glacial AcOH / toluene / 24 h

2: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

3: Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

4: dimethylformamide; dimethylsulfoxide / 1 h / 125 °C

5: 2.) p-toluenesulfonic acid / 1.) 1,2-dichlorobenzene, reflux, 16 h, 2.) 1,2-dichlorobenzene, 150 deg C, 45 min

6: 79 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: 88 percent / Et₃N, (diphenylphosphino)ethane, Pd(OAc)2 / dimethylsulfoxide; methanol / 48 h / 70 - 80 °C

8: 99 percent / LiBH₄ / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; palladium diacetate; lithium aluminium tetrahydride; lithium borohydride; sodium acetate; toluene-4-sulfonic acid; acetic acid; triethylamine; ethyl-diphenyl-phosphane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00071a008