(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

Base Information

Chemical Name:(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane
CAS No.:142459-43-6
Molecular Formula:C₁₁H₁₉NO
Molecular Weight:181.278
Hs Code.:

Synonyms:(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

Chemical Property:

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Technology Process of (1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

There total 24 articles about (1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane 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: 74.0%

: 130607-97-5
(4R,4aR,5S,8aR)-4,5-Dimethyl-3-oxoperhydroisochroman

: 142459-43-6
(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

Guidance literature:: With dimethylaluminium amide; In hexane; dichloromethane; xylene; 1) r.t., 1 h, 2) 95 deg C, 3) 95 deg C - 100 deg C, 24 h;
DOI:10.1021/jo00036a026

Reference yield:

: 124908-76-5,130607-96-4,142560-65-4
(1S,2S,3S)-1-<<(tert-Butyldimethylsilyl)oxy>-methyl>-2-<(1R)-1-cyanoethyl>-3-methylcyclohexane

: 142459-43-6
(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 ℃; for 0.75h;
DOI:10.1021/jo00036a026

Reference yield:

: 124908-72-1
3-<<(tert-Butyldimethylsilyl)oxy>methyl>-1-methoxy-5-methyl-1,4-cyclohexadiene

: 142459-43-6
(1R,2S,3S)-2-<(R)-1-Cyanoethyl>-1-(hydroxymethyl)-3-methylcyclohexane

Guidance literature:: Multi-step reaction with 10 steps

1: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

2: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

3: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

4: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

5: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

6: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

7: 72 percent / H₂ / 10percent Pd/C / ethanol

8: ethanol / 1.5 h / Heating

9: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

10: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dichloromaleic acid anhydride; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; hydrogen; sodium methylate; sodium acetate; p-toluenesulfonyl chloride; lithium chloride; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; acetonitrile;
DOI:10.1021/jo00036a026