(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

Base Information

Chemical Name:(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester
CAS No.:809286-04-2
Molecular Formula:C₂₀H₂₄FNO₃
Molecular Weight:345.414
Hs Code.:

Synonyms:(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

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Chemical Property of (R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

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Technology Process of (R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

There total 6 articles about (R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester 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: 53.0%

: 22556-08-7
trans-3,4-caranediol

: 253178-33-5
(+/-)-α-cyano-α-fluoro-p-tolylacetyl chloride

: 809286-04-2
(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

: 809286-03-1
(S)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/ol0479489

Reference yield:

: 2947-61-7
(4-methylphenyl)acetonitrile

: 809286-04-2
(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / NaH / tetrahydrofuran / 2 h / Heating

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 95 percent / FClO₃ / tetrahydrofuran / 2 h / 20 °C

3.1: 731 mg / LiOH / tetrahydrofuran; H₂O / 0.33 h / 20 °C

4.1: 519 mg / (COCl)2; DMF / CH₂Cl₂ / 3 h / 20 °C

5.1: 53 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; lithium hydroxide; oxalyl dichloride; sodium hydride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0479489

Reference yield:

: 147795-55-9,39266-20-1
ethyl 2-cyano-2-(p-tolyl)acetate

: 809286-04-2
(R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 95 percent / FClO₃ / tetrahydrofuran / 2 h / 20 °C

2.1: 731 mg / LiOH / tetrahydrofuran; H₂O / 0.33 h / 20 °C

3.1: 519 mg / (COCl)2; DMF / CH₂Cl₂ / 3 h / 20 °C

4.1: 53 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

With pyridine; lithium hydroxide; oxalyl dichloride; sodium hydride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0479489