[(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester
• CAS No.: 1245079-22-4
• Molecular Formula: C₁₅H₂₀F₂N₂O₂
• Molecular Weight: 298.333
• Mol file: 1245079-22-4.mol

Synonyms:[(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Chemical Property of [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

Chemical Property:

• Boiling Point: 381.8±42.0 °C(Predicted)
• Density: 1.20±0.1 g/cm3(Predicted)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

There total 11 articles about [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester 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:

[(3R,4S)-1-benzyl-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (1245079-21-3) → [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (1245079-22-4)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In industrial methylated spirits; toluene; at 20 - 60 ℃; for 78h;

Reference yield:

2,5-difluorobenzaldehyde (2646-90-4) → [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (1245079-22-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide / water; methanol / 0.67 h / 4 - 6 °C

1.2: Cooling with ice

2.1: dmap / 18 h / 0 - 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 1 h / -5 - 30 °C

4.1: hydrogen / RaNi / industrial methylated spritis / 18 h / 20 °C / 37503.8 Torr / Autoclave

5.1: di-tert-butyl dicarbonate / tetrahydrofuran / 18 h / 0 - 20 °C

6.1: isopropyl alcohol; diethyl ether; 2-Methylpentane / Resolution of racemate; Autoclave

7.1: hydrogen / palladium 10% on activated carbon / toluene; industrial methylated spirits / 78 h / 20 - 60 °C

With dmap; di-tert-butyl dicarbonate; hydrogen; trifluoroacetic acid; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; methanol; industrial methylated spirits; diethyl ether; 2-Methylpentane; dichloromethane; industrial methylated spritis; water; isopropyl alcohol; toluene;

Reference yield:

1-(2,5-difluorophenyl)-2-nitroethanol (951127-26-7) → [(3R,4S)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (1245079-22-4)

Guidance literature:

Multi-step reaction with 6 steps

1: dmap / 18 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 1 h / -5 - 30 °C

3: hydrogen / RaNi / industrial methylated spritis / 18 h / 20 °C / 37503.8 Torr / Autoclave

4: di-tert-butyl dicarbonate / tetrahydrofuran / 18 h / 0 - 20 °C

5: isopropyl alcohol; diethyl ether; 2-Methylpentane / Resolution of racemate; Autoclave

6: hydrogen / palladium 10% on activated carbon / toluene; industrial methylated spirits / 78 h / 20 - 60 °C

With dmap; di-tert-butyl dicarbonate; hydrogen; trifluoroacetic acid; palladium 10% on activated carbon; In tetrahydrofuran; industrial methylated spirits; diethyl ether; 2-Methylpentane; dichloromethane; industrial methylated spritis; isopropyl alcohol; toluene;

upstream raw materials:

2,5-difluorobenzaldehyde

1-(2,5-difluorophenyl)-2-nitroethanol

[(3R,4S)-1-benzyl-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

2,4,5-trifluorobenzaldehyde

Downstream raw materials:

[(3R,4S)-1-(5-cyanopyrimidin-2-yl)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

[(3S,4S)-1-(5-bromopyrimidin-2-yl)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

[(3R,4S)-1-(5-cyanopyrazin-2-yl)-4-(2,5-difluorophenyl)pyrrolidin-3-yl]carbamic acid tert-butyl ester

(R)-3-[(R)-1-(5-{2-[(3R,4S)-3-tert-butoxycarbonylamino-4-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrimidin-5-yl}-[1,2,4]oxadiazol-3-yl)ethoxy]pyrrolidine-1-carboxylic acid isopropyl ester