(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine

Base Information

• Chemical Name: (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine
• CAS No.: 220047-80-3
• Molecular Formula: C₁₉H₂₆N₂O₃
• Molecular Weight: 330.427
• Mol file: 220047-80-3.mol

Synonyms:(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine

Chemical Property of (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine

There total 14 articles about (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine 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: 96.0%

potassium cyanide (151-50-8) + (2S,4R)-2-Benzyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (220047-71-2) → (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine (220047-80-3)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃; for 3h;

DOI:10.1016/S0040-4020(98)00989-2

Reference yield:

(R)-2-amino-3-benzyloxypropyl phenyl sulfone (220047-55-2) → (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine (220047-80-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) titanium(IV) isopropoxide, 2.) NaBH₃CN / 1.) EtOH, room temp., 1 h, 2.) EtOH, overnight

2: 63 percent / K₂CO₃ / dimethylformamide / 48 h / 80 °C

3: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature

4: 85 percent / pyridine / 24 h / 0 °C

5: 99 percent / K₂CO₃ / dimethylformamide; H₂O / 24 h / Ambient temperature

6: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C

7: 95 percent / H₂ / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

8: 100 percent / Na-Hg, Na₂HPO₄ / methanol / 2 h / 0 °C

9: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h

10: 96 percent / dimethylsulfoxide / 3 h / 80 °C

With titanium(IV) isopropylate; hydrogenchloride; dmap; disodium hydrogenphosphate; sodium amalgam; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(98)00989-2

Reference yield:

(R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone (175229-12-6) → (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-cyanomethylpyrrolidine (220047-80-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / aq. HCl / ethyl acetate / 2 h / Ambient temperature

2: 1.) titanium(IV) isopropoxide, 2.) NaBH₃CN / 1.) EtOH, room temp., 1 h, 2.) EtOH, overnight

3: 63 percent / K₂CO₃ / dimethylformamide / 48 h / 80 °C

4: 94 percent / aq. HCl / tetrahydrofuran / 3 h / Ambient temperature

5: 85 percent / pyridine / 24 h / 0 °C

6: 99 percent / K₂CO₃ / dimethylformamide; H₂O / 24 h / Ambient temperature

7: 73 percent / Ti(O-i-Pr)4, KHMDS / tetrahydrofuran; toluene / 2 h / -70 °C

8: 95 percent / H₂ / Pd/C / methanol / 3 h / 760 Torr / Ambient temperature

9: 100 percent / Na-Hg, Na₂HPO₄ / methanol / 2 h / 0 °C

10: 85 percent / DMAP / pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 24 h

11: 96 percent / dimethylsulfoxide / 3 h / 80 °C

With titanium(IV) isopropylate; hydrogenchloride; dmap; disodium hydrogenphosphate; sodium amalgam; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(98)00989-2

upstream raw materials:

potassium cyanide

(2S,4R)-2-Benzyloxymethyl-4-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

benzyl bromide

(R)-3-benzyloxy-2-(tert-butoxycarbonylamino)propyl phenyl sulfone

Downstream raw materials:

(2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-[2'-N-(tert-butoxycarbonyl)amino]ethylpyrrolidine