(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

Base Information

Chemical Name:(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol
CAS No.:1222136-77-7
Molecular Formula:C₁₆H₁₇NO₂
Molecular Weight:255.316
Hs Code.:

Synonyms:(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

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Chemical Property of (1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

Chemical Property:

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Technology Process of (1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

There total 17 articles about (1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol 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:

: (±)-trans-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

: 1222136-77-7
(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

: 1222136-74-4
[(1S,2S)-2-(5-(benzyloxy)pyridin-3-yl)cyclopropyl]methanol

Guidance literature:: With Chiralpak AD-H; In methanol; at 40 ℃; Resolution of racemate;

Reference yield:

: 625-92-3
3,5-dibromopyridine

: 1222136-77-7
(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 20 °C / Inert atmosphere

2.1: phenyl carbamate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 4 h / 130 °C / Inert atmosphere

3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

5.1: sodium hydride / dimethyl sulfoxide / 1.17 h / Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 2 h / -78 - -20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / methanol / 3.25 h / 0 - 20 °C / Inert atmosphere

8.1: Chiralpak AD-H / ethanol / Resolution of racemate

With dmap; sodium tetrahydroborate; phenyl carbamate; water; palladium diacetate; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 2.1: Heck reaction / 5.1: Corey-Chaykowsky cyclopropanation reaction / 5.2: Corey-Chaykowsky cyclopropanation reaction;
DOI:10.1021/jm201157c

Reference yield:

: 130722-95-1
3-(benzyloxy)-5-bromopyridine

: 1222136-77-7
(1R,2R)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: phenyl carbamate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 4 h / 130 °C / Inert atmosphere

2.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

4.1: sodium hydride / dimethyl sulfoxide / 1.17 h / Inert atmosphere

4.2: 2 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2 h / -78 - -20 °C / Inert atmosphere

6.1: sodium tetrahydroborate / methanol / 3.25 h / 0 - 20 °C / Inert atmosphere

7.1: Chiralpak AD-H / ethanol / Resolution of racemate

With dmap; sodium tetrahydroborate; phenyl carbamate; water; palladium diacetate; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Heck reaction / 4.1: Corey-Chaykowsky cyclopropanation reaction / 4.2: Corey-Chaykowsky cyclopropanation reaction;
DOI:10.1021/jm201157c