(2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine

Base Information

• Chemical Name: (2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine
• CAS No.: 61478-29-3
• Molecular Formula: C29H29 N P2
• Molecular Weight: 453.503
• Hs Code.: 2933990090
• European Community (EC) Number: 634-714-4
• DSSTox Substance ID: DTXSID701155302
• Nikkaji Number: J25.971C
• Wikidata: Q76416269
• Mol file: 61478-29-3.mol

Synonyms:61478-29-3;(2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine;(2S,4S)-4-(Diphenylphosphino)-2-((diphenylphosphino)methyl)pyrrolidine;[(3S,5S)-5-(diphenylphosphanylmethyl)pyrrolidin-3-yl]-diphenylphosphane;(2S,4S)-4-(diphenylphosphanyl)-2-((diphenylphosphanyl)methyl)pyrrolidine;Pyrrolidine, 4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-,(2S,4S)-;(2s,4s)-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine;SCHEMBL927238;PQHKXSOICTYGQD-OUTSHDOLSA-N;DTXSID701155302;77450-05-6;MFCD00010275;MFCD01630791;AKOS015895726;CS-0085886;A833253;(2S,4S)-(-)-Diphenylphosphino 2-diphenylphosphinomethyl pyrrolidine;(2s,4s)-4-diphenylphosphino-2-diphenylphosphino-methylpyrrolidine;(2S,4S)-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine;(2S,4S)-(-)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino) pyrrolidine;(2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl) pyrrolidine;2alpha-(Diphenylphosphinomethyl)-4alpha-(diphenylphosphino)pyrrolidine;(2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4- (diphenylphosphino) pyrrolidine;(2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine, >=98.0% (CHN)

Chemical Property of (2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 102-104 ºC
• Boiling Point: 575.753°C at 760 mmHg
• PKA: 9.87±0.10(Predicted)
• Flash Point: 302.005°C
• PSA: 39.21000
• LogP: 5.31150
• Storage Temp.: 0-6°C
• Sensitive.: air sensitive
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 453.17752392
• Heavy Atom Count: 32
• Complexity: 493

Purity/Quality:

98%min ^*data from raw suppliers

(2S,4S)-(-)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino)pyrrolidine, min. 97% (S,S-PPM) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC1CP(C2=CC=CC=C2)C3=CC=CC=C3)P(C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: C1[C@@H](CN[C@@H]1CP(C2=CC=CC=C2)C3=CC=CC=C3)P(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of (2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine

There total 9 articles about (2S,4S)-(-)-4-Diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine 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: 94.0%

(2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine (61478-28-2) → (2S,4S)-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine (61478-29-3)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 1h;

DOI:10.1021/jo01311a036

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → (2S,4S)-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine (61478-29-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 69.6 percent / Et₃N / dioxane; H₂O / 15 h / 50 °C

2: 81 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 15 h

3: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days

4: 63.5 percent / 1.) Na/NH₃ (liq.) / 1.) THF, temperature of liquid NH₃, 2.) room temperature, 18.5 h

5: CF₃COOH / 0.5 h / 0 °C

With lithium aluminium tetrahydride; ammonia; sodium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; water;

DOI:10.1021/jo00327a023

Reference yield:

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate (61478-26-0) → (2S,4S)-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine (61478-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 1.) 0 deg C, 2.) stored in the refrigerator for 5 days

2: 63.5 percent / 1.) Na/NH₃ (liq.) / 1.) THF, temperature of liquid NH₃, 2.) room temperature, 18.5 h

3: CF₃COOH / 0.5 h / 0 °C

With ammonia; sodium; trifluoroacetic acid; In pyridine;

DOI:10.1021/jo00327a023

upstream raw materials:

(2S,4S)-N-butoxycarbonyl-4-diphenylphosphino-2-diphenylphosphinomethylpyrrolidine

(2S,4S)-N-(tert-butoxycarbonyl)-4-(p-toluenesulfonyloxy)-2-<(p-toluenesulfonyloxy)methyl>pyrrolidine

trans-4-hydroxy-L-proline ethyl ester hydrochloride

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

Downstream raw materials:

(2S,4S)-4-(Diphenylphosphino)-2-<(diphenylphosphino)-methyl>-N-pivaloylpyrrolidine

CBZ-(S)-Pro-PPM

(2S,4S)-4-Diphenylphosphanyl-2-[(diphenylphosphanyl)-methyl]-pyrrolidine-1-carboxylic acid (4-chloro-phenyl)-amide

N-[(2S,4S)-(-)-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidyne]-N'-(2,3,6,2',3',4',6'-hexa-O-acetyl-β-D-cellobiose)urea

Refernces

• 1、 Ishizuka, Naoyasu,Togashi, Masahiro,Inoue, Masami,Enomoto, Saburo. "Asymmetric Hydrogenation of 3,4-Methylenedioxy-α-acetamidocinnamic Acid Using Newly Developed Silica Gel-Supported Chiral Rhodium(I)-Phosphine Complexes". . p. 1686 - 1690. Retrieved 2007/10/02.
• 2、 Ojima, Iwao,Kogure, Tetsuo,Yoda, Noriko. "Asymmetric Hydrogenation of Prochiral Olefins Catalyzed by Rhodium Complexes with Chiral Pyrrolidinodiphosphines. Crucial Factors for the Effective Asymmetric Induction". . p. 4728 - 4739. Retrieved 2007/10/02.