3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

Base Information

Chemical Name:3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine
CAS No.:1222137-99-6
Molecular Formula:C₂₄H₃₀N₂O₄
Molecular Weight:410.513
Hs Code.:

Synonyms:3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

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Chemical Property of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

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Technology Process of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

There total 10 articles about 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine 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: 90.0%

: 1222137-97-4
5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]-3-pyridinol

: 161511-85-9
2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester

: 1222137-99-6
3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

Guidance literature:: With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In toluene; at 20 ℃; Cooling with ice;

Reference yield:

: 1222136-50-6
trans-3-[5-(benzyloxy)-3-pyridyl]acrylic acid n-butyl ester

: 1222137-99-6
3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

Guidance literature:: Multi-step reaction with 10 steps

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

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

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

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

4.2: 3.5 h / 20 °C

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

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

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

8.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve; Cooling with ice

9.1: hydrogen; palladium / methanol; ethyl acetate / 2 h

10.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / water; toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice

With sodium tetrahydroborate; oxalyl dichloride; diisobutylaluminum hydride; tributylphosphine; water; hydrogen; sodium hydride; palladium; triethylamine; sodium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; mineral oil;

Reference yield:

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

: 1222137-99-6
3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxyl]-5-[(1S,2S)-2-(phenoxymethyl)cyclopropyl]pyridine

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

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

4.2: 3.5 h / 20 °C

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

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

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

8.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve; Cooling with ice

9.1: hydrogen; palladium / methanol; ethyl acetate / 2 h

10.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / water; toluene / 0.17 h / 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice

With dmap; sodium tetrahydroborate; diisobutylaluminum hydride; tributylphosphine; phenyl carbamate; water; hydrogen; palladium diacetate; sodium hydride; potassium carbonate; palladium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;