(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate

Base Information

• Chemical Name: (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate
• CAS No.: 1222136-80-2
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.408
• Mol file: 1222136-80-2.mol

Synonyms:(1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate

Chemical Property of (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate

There total 12 articles about (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate 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: 94.0%

[(1S,2S)-2-(5-(benzyloxy)pyridin-3-yl)cyclopropyl]methanol (1222136-74-4) + 2-Methylpropionic anhydride (97-72-3) → (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate (1222136-80-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 2h; Cooling with ice;

DOI:10.1021/jm400510u

Reference yield: 94.0%

Isovaleric anhydride (1468-39-9) + [(1S,2S)-2-(5-(benzyloxy)pyridin-3-yl)cyclopropyl]methanol (1222136-74-4) → (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate (1222136-80-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jm3008739

Reference yield:

3,5-dibromopyridine (625-92-3) → (1S,2S)-2-[5-(benzyloxy)-3-pyridyl]cyclopropylmethyl isobutyrate (1222136-80-2)

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

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

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

6.2: 3.5 h / 20 °C

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

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

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

10.1: dmap; triethylamine / dichloromethane

10.2: 1.75 h / 0 °C / Cooling with ice

With dmap; sodium tetrahydroborate; oxalyl dichloride; diisobutylaluminum hydride; phenyl carbamate; water; palladium diacetate; sodium hydride; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

upstream raw materials:

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

2-Methylpropionic anhydride

Isovaleric anhydride

3,5-dibromopyridine

Downstream raw materials:

2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate