benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

Base Information

Chemical Name:benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate
CAS No.:777089-33-5
Molecular Formula:C₂₁H₂₄FNO₈S₂
Molecular Weight:501.554
Hs Code.:

Synonyms:benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

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Chemical Property of benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

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Technology Process of benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

There total 8 articles about benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate 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:

: 777089-32-4
benzyl 4-[2,3-bis(hydroxymethyl)cyclopropyl]-3-fluorophenylcarbamate

: 7143-01-3
Methanesulfonic anhydride

: 777089-33-5
benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/ol050730h

Reference yield:

: 777089-26-6
benzyl 3-fluoro-4-formylphenylcarbamate

: 777089-33-5
benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.33 h / 0 °C

1.2: 72 percent / dimethylformamide / 16 h / 0 - 20 °C

2.1: 92 percent / DIBALH / tetrahydrofuran / 1.5 h / -78 °C

3.1: Me₂CH=C(Cl)NMe₂ / CH₂Cl₂ / 0.67 h / 23 °C

3.2: 84 percent / N,N-dimethylaniline; Et₃N / CH₂Cl₂ / 0.75 h / 0 - 20 °C

4.1: 73 percent / bis(N-t-butylsalicylaldiminato)copper(II) / 1,2-dichloro-ethane; toluene / 1 h / Heating

5.1: 81 percent / LiBH₄ / tetrahydrofuran / 14 h / 0 - 20 °C

6.1: Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

With lithium borohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; sodium hydride; diisobutylaluminium hydride; triethylamine; bis(N-tert-butylsalicylaldiminato)copper(II); In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol050730h

Reference yield:

: 777089-29-9
benzyl 3-fluoro-4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate

: 777089-33-5
benzyl 4-[2,3-bis(methanesulfonyloxymethyl)cyclopropyl]-3-fluorophenylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Me₂CH=C(Cl)NMe₂ / CH₂Cl₂ / 0.67 h / 23 °C

1.2: 84 percent / N,N-dimethylaniline; Et₃N / CH₂Cl₂ / 0.75 h / 0 - 20 °C

2.1: 73 percent / bis(N-t-butylsalicylaldiminato)copper(II) / 1,2-dichloro-ethane; toluene / 1 h / Heating

3.1: 81 percent / LiBH₄ / tetrahydrofuran / 14 h / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

With lithium borohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; triethylamine; bis(N-tert-butylsalicylaldiminato)copper(II); In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;
DOI:10.1021/ol050730h