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

Base Information

Chemical Name:2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate
CAS No.:1222137-55-4
Molecular Formula:C₂₆H₃₄N₂O₆S
Molecular Weight:502.632
Hs Code.:

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

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

Chemical Property:

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

There total 22 articles about 2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate 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: 82.0%

: 1222137-51-0
2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethanol

: 98-59-9
p-toluenesulfonyl chloride

: 1222137-55-4
2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield: 82.0%

: 1222137-06-5
2-[(1R,2S)-2-[5-[[1-(tert-butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethanol

: 98-59-9
p-toluenesulfonyl chloride

: 1222137-55-4
2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

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

: 1222137-55-4
2-[(1S,2R)-2-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]cyclopropyl]ethyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 14 steps

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

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

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

3.2: 3.5 h / 20 °C

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

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

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

7.1: dmap; triethylamine / dichloromethane

7.2: 1.75 h / 0 °C / Cooling with ice

8.1: palladium 10% on activated carbon; hydrogen / methanol; water; ethyl acetate / 1.5 h / 20 °C / Cooling with ice

9.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 9 h / 0 - 20 °C / Inert atmosphere

10.1: methanol; sodium methylate / 6 h / 40 °C / Inert atmosphere

11.1: oxalyl dichloride; methyltriphenylphosphonium bromide/NaNH₂; triethylamine / diethyl ether; dichloromethane; dimethyl sulfoxide / 6.15 h / -70 - 20 °C / Cooling with ice; Inert atmosphere; Cooling with acetone-dry ice

12.1: triphenylphosphine / diethyl ether / 0.33 h / 0 °C / Cooling with ice

13.1: borane-THF; cyclohexene / tetrahydrofuran / 6.08 h / 20 °C / Inert atmosphere; Cooling with ice

13.2: 0.78 h / 55 °C

14.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

With methanol; dmap; sodium tetrahydroborate; borane-THF; oxalyl dichloride; diisobutylaluminum hydride; tributylphosphine; palladium 10% on activated carbon; methyltriphenylphosphonium bromide/NaNH₂; water; hydrogen; sodium methylate; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; sodium hydroxide; 1,1'-azodicarbonyl-dipiperidine; cyclohexene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; mineral oil; 9.1: |Mitsunobu Displacement;