(S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine

Base Information

• Chemical Name: (S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine
• CAS No.: 864466-71-7
• Molecular Formula: C₂₃H₃₃NOSi
• Molecular Weight: 367.607
• Hs Code.: 2933990090
• European Community (EC) Number: 687-887-3
• Nikkaji Number: J2.212.713F
• Wikidata: Q76422595
• Mol file: 864466-71-7.mol

Synonyms:864466-71-7;(S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine;tert-butyl-[diphenyl-[(2S)-pyrrolidin-2-yl]methoxy]-dimethylsilane;(S)-2-(((tert-Butyldimethylsilyl)-oxy)diphenylmethyl)pyrrolidine;MFCD09954370;(S)-[t-Butyldimethylsiloxy)-diphenylmethyl]pyrrolidine;SCHEMBL5521107;(S)-2-[(tert-Butyldimethylsiloxy)diphenylmethyl]pyrrolidine;AKOS016005480;DS-3813;s12241;AC-31762;CS-0091913;(S)-(?)-|A,|A-Diphenylprolinol tert-butyldimethylsilyl ether;(2S)-2-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]diphenylmethyl]pyrrolidine;(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol tert-butyldimethylsilyl ether, >=97% (HPLC)

Chemical Property of (S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine

Chemical Property:

• Melting Point: 71-73°C
• Boiling Point: 445.2±35.0 °C(Predicted)
• PKA: 10.12±0.10(Predicted)
• Flash Point: >110°C (>230°F)
• PSA: 12.47000
• Density: 0.998±0.06 g/cm3(Predicted)
• LogP: 4.33280
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 367.233141211
• Heavy Atom Count: 26
• Complexity: 426

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanol tert-butyldimethylsilyl ether ≥97% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 10368174
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC(C1CCCN1)(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: CC(C)(C)[Si](C)(C)OC([C@@H]1CCCN1)(C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of (S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine

There total 3 articles about (S)-2-(((tert-Butyldimethylsilyl)oxy)diphenylmethyl)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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + (R)-α,α-diphenylprolinol (22348-32-9) → (R)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine (1236033-34-3,864466-71-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 20h;

DOI:10.1021/acs.joc.1c01116

Reference yield: 82.0%

(S)-diphenylprolinol (22348-32-9,63401-04-7,112022-88-5,112068-01-6) + t-butyldimethylsiyl triflate (69739-34-0) → (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine (864466-71-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1021/ja511231f

Reference yield:

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + t-butyldimethylsiyl triflate (69739-34-0) + (S)-proline-N-ethyl carbamate methyl ester (77581-28-3,93423-88-2) + phenylmagnesium bromide (100-58-3) + 4-methoxyphenyl magnesium bromide (13139-86-1) → (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine (848821-58-9) + (S)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine (864466-71-7) + (S)-2-[(4-methoxyphenyl)-phenyl-trimethylsilyloxy-methyl]-pyrrolidine (1208864-96-3) + (S)-2-[(4-methoxyphenyl)-phenyl-tert-butyldimethylsilyloxy-methyl]-pyrrolidine (1208864-98-5) + (S)-2-[bis(4-methoxyphenyl)-trimethylsilyloxy-methyl]-pyrrolidine (1208864-97-4) + (S)-2-[bis(4-methoxyphenyl)-tert-butyldimethylsilyloxy-methyl]-pyrrolidine (1208864-99-6)

Guidance literature:

(S)-proline-N-ethyl carbamate methyl ester; phenylmagnesium bromide; 4-methoxyphenyl magnesium bromide; In tetrahydrofuran; at 0 ℃; for 3.5h; Inert atmosphere;

With potassium hydroxide; In methanol; for 24h; Reflux;

trimethylsilyl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1002/chem.200902449

upstream raw materials:

(S)-diphenylprolinol

t-butyldimethylsiyl triflate

trimethylsilyl trifluoromethanesulfonate

(S)-proline-N-ethyl carbamate methyl ester

Refernces

• 1、 Chang, Yejin,Cao, Min,Chan, Jessica Z.,Zhao, Cunyuan,Wang, Yuankai,Yang, Rose,Wasa, Masayuki. "Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst". supporting information. p. 2441 - 2455. Retrieved 2021/02/16.
• 2、 Fleischer, Ivana,Pfaltz, Andreas. "Enantioselective michael addition to α,β-Unsaturated aldehydes: Combinatorial catalyst preparation and screening, reaction optimization and mechanistic studies". supporting information; experimental part. p. 95 - 99. Retrieved 2010/03/26.