Butyl (2R,4R)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate

Base Information

• Chemical Name: Butyl (2R,4R)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate
• CAS No.: 72598-03-9
• Molecular Formula: C34H37 N O2 P2
• Molecular Weight: 553.61
• DSSTox Substance ID: DTXSID10703595
• Wikidata: Q82635790
• Mol file: 72598-03-9.mol

Synonyms:72598-03-9;BUTYL (2R,4R)-4-(DIPHENYLPHOSPHANYL)-2-[(DIPHENYLPHOSPHANYL)METHYL]PYRROLIDINE-1-CARBOXYLATE;butyl (2R,4R)-4-diphenylphosphanyl-2-(diphenylphosphanylmethyl)pyrrolidine-1-carboxylate;1-Pyrrolidinecarboxylicacid, 4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-, 1,1-dimethylethylester, (2R,4R)-;(R,R)-BPPM;(2R,4R)-BPPM;DTXSID10703595

Chemical Property of Butyl (2R,4R)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 638.8±40.0 °C(Predicted)
• PKA: -2.47±0.60(Predicted)
• PSA: 56.72000
• LogP: 6.56970
• Sensitive.: air sensitive
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 553.22995342
• Heavy Atom Count: 39
• Complexity: 674

Purity/Quality:

97% ^*data from raw suppliers

(2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino)-N-(t-butoxycarbonyl)pyrrolidine, min. 97% (R,R-BPPM) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCOC(=O)N1CC(CC1CP(C2=CC=CC=C2)C3=CC=CC=C3)P(C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: CCCCOC(=O)N1C[C@@H](C[C@@H]1CP(C2=CC=CC=C2)C3=CC=CC=C3)P(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of Butyl (2R,4R)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]pyrrolidine-1-carboxylate

There total 11 articles about Butyl (2R,4R)-4-(diphenylphosphanyl)-2-[(diphenylphosphanyl)methyl]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: 34.0%

N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate (77450-04-5) + diphenylphosphane (829-85-6) → N-(tert-Butoxycarbonyl)-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine (72598-03-9)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran;

DOI:10.1021/jo00327a023

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → N-(tert-Butoxycarbonyl)-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine (72598-03-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

3: 1.) Et₄NOAc*4H₂O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C

4: 45 percent / LiBH₄ / tetrahydrofuran

5: 69 percent / pyridine

6: 34 percent / 1.) Na/NH₃ (liq.) / tetrahydrofuran

With sodium hydroxide; lithium borohydride; tetraethylammonium acetate; ammonia; sodium; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

Reference yield:

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride (77449-99-1) → N-(tert-Butoxycarbonyl)-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine (72598-03-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

2: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h

3: 1.) Et₄NOAc*4H₂O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C

4: 45 percent / LiBH₄ / tetrahydrofuran

5: 69 percent / pyridine

6: 34 percent / 1.) Na/NH₃ (liq.) / tetrahydrofuran

With sodium hydroxide; lithium borohydride; tetraethylammonium acetate; ammonia; sodium; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

upstream raw materials:

N-(tert-Butoxycarbonyl)-4-hydroxy-D-prolinol Di-p-toluenesulfonate

diphenylphosphane

N-(tert-butyloxycarbonyl) azide

(2R,4R)-2-ethoxycarbonyl-4-hydroxypyrrolidine hydrochloride

Downstream raw materials:

N-Acryloyl-(2R,4R)-4-(diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine

(2R,4R)-4-(Diphenylphosphino)-2-<(diphenylphosphino)methyl>pyrrolidine