(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

Base Information

Chemical Name:(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide
CAS No.:756900-00-2
Molecular Formula:C₂₁H₃₅NO₂
Molecular Weight:333.514
Hs Code.:

Synonyms:(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

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Chemical Property of (2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

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Technology Process of (2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

There total 9 articles about (2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide 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: 94.0%

: 74-88-4
methyl iodide

: 756899-99-7
(2S)-N-((3R,5S)-3,5-dimethyl-6-benzyloxyhexyl)-2-methylbutyramide

: 756900-00-2
(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

Guidance literature:: (2S)-N-((3R,5S)-3,5-dimethyl-6-benzyloxyhexyl)-2-methylbutyramide; With sodium hydride; In tetrahydrofuran; at -78 ℃; for 0.333333h;

methyl iodide; In tetrahydrofuran; at 20 ℃; for 20h; Further stages.;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 108814-35-3
(2R,3R,4S)-1-(benzyloxy)-2,4-dimethyl-3-hydroxy-5-hexene

: 756900-00-2
(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

Guidance literature:: Multi-step reaction with 10 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

2.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

3.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

4.1: 68 percent / n-Bu₃SnH; AIBN / 0.33 h / 100 °C

5.1: 87 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 11 h / 20 °C

7.1: 88 percent / NaN₃ / dimethylformamide / 20 - 50 °C

8.1: H₂ / Pd/C; Pb/CaCO₃ / ethanol / 1 h / 760.05 Torr

9.1: 97 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 4.25 h / 0 - 20 °C

10.1: NaH / tetrahydrofuran / 0.33 h / -78 °C

10.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; palladium on activated charcoal; Piperonyl butoxide; calcium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014

Reference yield:

: 134961-82-3
(2R,3S,4S)-1-benzyloxy-2,4-dimethyl-3,6-hexanediol

: 756900-00-2
(2S)-N-methyl-N-((3R,5S)-3,5-dimethyl-6-benzyloxy-hexyl)-2-methylbutyramide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 78 percent / imidazole / dimethylformamide / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 87 percent / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C

3.1: 68 percent / n-Bu₃SnH; AIBN / 0.33 h / 100 °C

4.1: 87 percent / n-Bu₄NF / tetrahydrofuran / 0 - 20 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 11 h / 20 °C

6.1: 88 percent / NaN₃ / dimethylformamide / 20 - 50 °C

7.1: H₂ / Pd/C; Pb/CaCO₃ / ethanol / 1 h / 760.05 Torr

8.1: 97 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 4.25 h / 0 - 20 °C

9.1: NaH / tetrahydrofuran / 0.33 h / -78 °C

9.2: 94 percent / tetrahydrofuran / 20 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); diethyl cyanophosphonate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hydride; triethylamine; palladium on activated charcoal; Piperonyl butoxide; calcium carbonate; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.014