(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

Base Information

Chemical Name:(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile
CAS No.:150930-72-6
Molecular Formula:C₁₉H₃₅NOSi
Molecular Weight:321.579
Hs Code.:

Synonyms:(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

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Chemical Property of (1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

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Technology Process of (1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

There total 14 articles about (1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile 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: 85.0%

: 151-50-8
potassium cyanide

: 156210-32-1
Methanesulfonic acid 3-[(1R,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1,6-dimethyl-cyclohex-2-enyl]-propyl ester

: 150930-62-4
(1R,6S)-2-(hydroxymethyl)-1,6-dimethyl-2-cyclohexene-1-butyronitrile

: 150930-72-6
(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

Guidance literature:: With 18-crown-6 ether; In N,N-dimethyl-formamide; at 45 ℃; for 16h;
DOI:10.1021/ja00087a023

Reference yield:

: 105088-15-1
(4aR,5S)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

: 150930-72-6
(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / p-TsOH / dimethylformamide; methanol / 24 h

2: 1.) MCPBA, 2.) silica gel / 1.) benzene, hexanes, 0 deg C - RT, 30 min, 2.) benzene, hexanes, 40 min

3: 59 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4: 91 percent / imidazole / dimethylformamide / 2 h

5: 98 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

6: 81 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 85 percent / 18-crown-6 / dimethylformamide / 16 h / 45 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; silica gel; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00087a023

Reference yield:

: 150930-70-4
C₁₄H₂₂S₂

: 150930-72-6
(1R,6S)-2-<(tert-butyldimethylsiloxy)methyl>-1,6-dimethyl-2-cyclohexene-1-butyronitrile

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / aq. Tl(NO₃)3 / methanol; tetrahydrofuran / 0.17 h

2: 89 percent / p-TsOH / dimethylformamide; methanol / 24 h

3: 1.) MCPBA, 2.) silica gel / 1.) benzene, hexanes, 0 deg C - RT, 30 min, 2.) benzene, hexanes, 40 min

4: 59 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5: 91 percent / imidazole / dimethylformamide / 2 h

6: 98 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

7: 81 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: 85 percent / 18-crown-6 / dimethylformamide / 16 h / 45 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 18-crown-6 ether; silica gel; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; thallium(III) nitrate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00087a023