3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

Base Information

Chemical Name:3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester
CAS No.:334792-38-0
Molecular Formula:C₁₈H₂₂N₄O₃
Molecular Weight:342.398
Hs Code.:

Synonyms:3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

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Chemical Property of 3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

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Technology Process of 3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

There total 11 articles about 3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl 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: 45.0%

: 334792-37-9
ethyl 3-{(4R)-amino-(3R)-hydroxypiperidin-1-yl}benzoate

: 4595-60-2
2-bromopyrimidine

: 334792-38-0
3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 120 ℃; for 14h;
DOI:10.1016/j.bmc.2006.01.062

Reference yield:

: 334792-31-3
Ethyl 3-{(3R,4S)-3,4-(dihydroxy)-piperidin-1-yl}benzoate

: 334792-38-0
3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 30 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 3 h / 20 °C

2: 67 percent / triethylamine / CH₂Cl₂ / 0.08 h / 20 °C

3: 100 percent / sodium azide / dimethylformamide / 10 h / 90 °C

4: 100 percent / sodium ethoxide / tetrahydrofuran / 3.5 h / 30 °C

5: 100 percent / hydrogen / Pd/C / dioxane; H₂O / 3 h / 20 °C

6: 45 percent / ethyldiisopropylamine / dimethylsulfoxide / 14 h / 120 °C

With sodium azide; hydrogen; sodium ethanolate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.01.062

Reference yield:

: 3-[(3S,4R)-3,4,5-Trihydroxy-pent-(E)-ylideneamino]-benzoic acid ethyl ester

: 334792-38-0
3-[(3R,4R)-3-Hydroxy-4-(pyrimidin-2-ylamino)-piperidin-1-yl]-benzoic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 2.2 g / acetic acid; sodium cyanoborohydride / methanol; CH₂Cl₂ / 4 h / 20 °C

2: carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 0 - 20 °C

3: 160 mg / tetrahydrofuran / 2 h / 20 °C

4: 30 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 3 h / 20 °C

5: 67 percent / triethylamine / CH₂Cl₂ / 0.08 h / 20 °C

6: 100 percent / sodium azide / dimethylformamide / 10 h / 90 °C

7: 100 percent / sodium ethoxide / tetrahydrofuran / 3.5 h / 30 °C

8: 100 percent / hydrogen / Pd/C / dioxane; H₂O / 3 h / 20 °C

9: 45 percent / ethyldiisopropylamine / dimethylsulfoxide / 14 h / 120 °C

With sodium azide; carbon tetrabromide; hydrogen; sodium ethanolate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2006.01.062