1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea

Base Information

• Chemical Name: 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea
• CAS No.: 532399-55-6
• Molecular Formula: C₂₅H₃₂N₂O₂
• Molecular Weight: 392.541

Synonyms:

Chemical Property of 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea

There total 18 articles about 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea 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:

2-allyl-3-hydroxybenzoic acid ethyl ester (53596-59-1) → 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea (532399-55-6)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

2.1: 74 percent / OsO₄; aq. NaIO₄ / ethyl acetate / 20 °C

3.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

4.1: BH₃ / tetrahydrofuran

4.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

5.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

6.1: 86 percent / n-BuLi / tetrahydrofuran

7.1: 99 percent / H₂ / Pd/C / ethyl acetate

8.1: 99 percent / DIBAL-H / toluene / -78 °C

9.1: 98 percent / tetrahydrofuran / Heating

10.1: 100 percent / HCl / ethanol / 20 °C

11.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

12.1: 96 percent / aq. NaOH / methanol / Heating

13.1: SOCl₂ / CH₂Cl₂ / Heating

14.1: NaH / toluene / 0 - 25 °C

15.1: 76 percent / Pd(OAc)2 / CH₂Cl₂ / 0 - 25 °C

16.1: 93 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

17.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 25 °C

18.1: 98 percent / NH₂OH*HCl; NaOH / tetrahydrofuran / Heating

19.1: 84 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

20.1: benzene

With hydrogenchloride; palladium diacetate; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; borane; hydroxylamine hydrochloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; benzene; 5.1: Swern oxidation / 6.1: Wittig reaction / 9.1: Wittig reaction / 11.1: Mitsunobu reaction / 17.1: Swern oxidation;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea (532399-55-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 86 percent / n-BuLi / tetrahydrofuran

2: 99 percent / H₂ / Pd/C / ethyl acetate

3: 99 percent / DIBAL-H / toluene / -78 °C

4: 98 percent / tetrahydrofuran / Heating

5: 100 percent / HCl / ethanol / 20 °C

6: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

7: 96 percent / aq. NaOH / methanol / Heating

8: SOCl₂ / CH₂Cl₂ / Heating

9: NaH / toluene / 0 - 25 °C

10: 76 percent / Pd(OAc)2 / CH₂Cl₂ / 0 - 25 °C

11: 93 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

12: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 25 °C

13: 98 percent / NH₂OH*HCl; NaOH / tetrahydrofuran / Heating

14: 84 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

15: benzene

With hydrogenchloride; palladium diacetate; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; hydroxylamine hydrochloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; toluene; benzene; 1: Wittig reaction / 4: Wittig reaction / 6: Mitsunobu reaction / 12: Swern oxidation;

DOI:10.1016/j.bmcl.2005.01.015

Reference yield:

ethyl 3-(Methoxymethoxy)-2-prop-2-enylbenzoate (532399-59-0) → 1-Ethyl-3-{(1R,2R)-2-[(R)-2-(4-phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropylmethyl}-urea (532399-55-6)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 74 percent / OsO₄; aq. NaIO₄ / ethyl acetate / 20 °C

2.1: (-)-B-methoxydisopinocampheylborane / diethyl ether

3.1: BH₃ / tetrahydrofuran

3.2: 75 percent / aq. H₂O₂; NaOH / tetrahydrofuran

4.1: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

5.1: 86 percent / n-BuLi / tetrahydrofuran

6.1: 99 percent / H₂ / Pd/C / ethyl acetate

7.1: 99 percent / DIBAL-H / toluene / -78 °C

8.1: 98 percent / tetrahydrofuran / Heating

9.1: 100 percent / HCl / ethanol / 20 °C

10.1: 95 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 - 25 °C

11.1: 96 percent / aq. NaOH / methanol / Heating

12.1: SOCl₂ / CH₂Cl₂ / Heating

13.1: NaH / toluene / 0 - 25 °C

14.1: 76 percent / Pd(OAc)2 / CH₂Cl₂ / 0 - 25 °C

15.1: 93 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

16.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 25 °C

17.1: 98 percent / NH₂OH*HCl; NaOH / tetrahydrofuran / Heating

18.1: 84 percent / LiAlH₄ / tetrahydrofuran / 0 - 25 °C

19.1: benzene

With hydrogenchloride; palladium diacetate; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; oxalyl dichloride; borane; hydroxylamine hydrochloride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (-)-B-methoxydiisopinocampheylborane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; toluene; benzene; 4.1: Swern oxidation / 5.1: Wittig reaction / 8.1: Wittig reaction / 10.1: Mitsunobu reaction / 16.1: Swern oxidation;

DOI:10.1016/j.bmcl.2005.01.015

upstream raw materials:

ethyl isocyanate

C-{(1R,2R)-2-[(R)-2-(4-Phenyl-butyl)-2,3-dihydro-benzofuran-4-yl]-cyclopropyl}-methylamine

2-allyl-3-hydroxybenzoic acid ethyl ester

benzyltriphenylphosphonium bromide

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