5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

Base Information

Chemical Name:5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol
CAS No.:1222138-09-1
Molecular Formula:C₁₆H₁₇NO₂
Molecular Weight:255.316
Hs Code.:

Synonyms:5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

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Chemical Property of 5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

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Technology Process of 5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

There total 10 articles about 5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol 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: 84.0%

: 1222138-07-9
3-(benzyloxy)-5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]pyridine

: 1222138-09-1
5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

Guidance literature:: With hydrogen; palladium 10% on activated carbon; In methanol; ethyl acetate; for 4h;

Reference yield:

: 625-92-3
3,5-dibromopyridine

: 1222138-09-1
5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium hydride / hexane; N,N-dimethyl-formamide / 2.08 h / 20 °C / Inert atmosphere; Cooling with ice

1.2: 15 h / 20 °C / Inert atmosphere

2.1: phenyl carbamate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 4.17 h / 130 °C / Reflux; Inert atmosphere

3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 40 °C

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C

5.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.42 h / Inert atmosphere

5.2: 3.5 h / 20 °C

6.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / 1.42 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice

7.1: sodium tetrahydroborate / methanol / 0.58 h / Cooling with ice

8.1: Chiralpak AD-H / methanol / 40 °C / Resolution of racemate

9.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 4 h

With dmap; sodium tetrahydroborate; diisobutylaluminum hydride; phenyl carbamate; palladium 10% on activated carbon; water; hydrogen; palladium diacetate; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

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

: 1222138-09-1
5-[(1S,2S)-2-(benzyloxymethyl)cyclopropyl]-3-pyridinol

Guidance literature:: Multi-step reaction with 10 steps

1.1: phenyl carbamate; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 4.17 h / 130 °C / Reflux; Inert atmosphere

2.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 40 °C

3.1: oxalyl dichloride / dichloromethane / 0.22 h / 20 °C

4.1: triethylamine / dichloromethane / 0.62 h / 20 °C

5.1: sodium hydride / dimethyl sulfoxide; mineral oil / 0.42 h / Inert atmosphere

5.2: 3.5 h / 20 °C

6.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / 1.42 h / -78 °C / Inert atmosphere; Cooling with acetone-dry ice

7.1: sodium tetrahydroborate / methanol / 0.58 h / Cooling with ice

8.1: Chiralpak AD-H / methanol / 40 °C / Resolution of racemate

9.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 20 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 4 h

With sodium tetrahydroborate; oxalyl dichloride; diisobutylaluminum hydride; phenyl carbamate; palladium 10% on activated carbon; water; hydrogen; palladium diacetate; sodium hydride; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;