tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate
• CAS No.: 305329-97-9
• Molecular Formula: C10H18BrNO2
• Molecular Weight: 264.162
• Hs Code.: 2933990090
• Mol file: 305329-97-9.mol

Synonyms:3-Bromomethylpyrrolidine-1-carboxylicacid tert-butyl ester;

Chemical Property of tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 300.053 °C at 760 mmHg
• PKA: -2.14±0.40(Predicted)
• Flash Point: 135.268 °C
• PSA: 29.54000
• Density: 1.313 g/cm³
• LogP: 2.57620
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl3-(Bromomethyl)pyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate

There total 5 articles about tert-Butyl 3-(bromomethyl)pyrrolidine-1-carboxylate 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: 78.0%

3-trifluoromethanesulfonyloxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (305329-96-8) → 3-bromomethylpyrrolidine-1-carboxylic acid tert-butyl ester (305329-97-9)

Guidance literature:

With lithium bromide; In acetone; Heating;

DOI:10.1016/j.bmc.2003.12.039

Reference yield: 55.0%

tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (114214-69-6) → 3-bromomethylpyrrolidine-1-carboxylic acid tert-butyl ester (305329-97-9)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 18h;

Reference yield:

1-(Phenylmethyl)-3-pyrrolidinemethanol (5731-17-9) → 3-bromomethylpyrrolidine-1-carboxylic acid tert-butyl ester (305329-97-9)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium formate / Pd/C / methanol / 0.25 h / Heating

2: 3.82 g / K₂CO₃ / tetrahydrofuran; H₂O / 0 - 20 °C

3: 97 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 78 percent / LiBr / acetone / Heating

With ammonium formate; potassium carbonate; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1016/j.bmc.2003.12.039

upstream raw materials:

3-trifluoromethanesulfonyloxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

pyrrolidin-3-ylmethanol

1-(Phenylmethyl)-3-pyrrolidinemethanol

1-benzyl-5-oxopyrrolidine-3-carboxylic acid

Refernces

• 1、 -. "METHODS OF USE FOR INHIBITORS OF AKT ACTIVITY". Page/Page column 46. . Retrieved 2008/12/04.
• 2、 Polla, Magnus O.,Tottie, Louise,Norden, Carita,Linschoten, Marcel,Muesil, Djordje,Trumpp-Kallmeyer, Susanne,Aukrust, Inger R.,Ringom, Rune,Holm, Kjetil H.,Neset, Siren M.,Sandberg, Marcel,Thurmond, John,Yu, Peng,Hategan, Georgeta,Anderson, Herb. "Design and synthesis of potent, orally active, inhibitors of carboxypeptidase U (TAFIa)". . p. 1151 - 1175. Retrieved 2007/10/03.