943757-71-9

Basic information

• Product Name: Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-
• Synonyms: Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-;(diphenyl(trimethylsilyloxy)methyl)pyrrolidine;R-Diphenylprolinol trimethyl silyl ether;(2R)-2-[Diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine;(R)-(+)-a,a-Diphenyl-2-pyrrolidineMethanol TriMethylsilyl Ether;(R)-(+)-α,α-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 96%;(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidineMethanol triMethylsilyl ether 96%;(R)-2-[Diphenyl(trimethylsilanyloxy)methyl]pyrrolidine
• CAS NO: 943757-71-9
• Molecular Formula: C₂₀H₂₇NOSi
• Molecular Weight: 325.525
• Mol File: 943757-71-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 412.7 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.021
• Refractive Index: n20/D1.5509
• Storage Temp.: 2-8°C
• PKA: 10.01±0.10(Predicted)
• CAS DataBase Reference: Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-(943757-71-9)
• EPA Substance Registry System: Pyrrolidine, 2-[diphenyl[(trimethylsilyl)oxy]methyl]-, (2R)-(943757-71-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 943757-71-9(Hazardous Substances Data)

Usage

Uses

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether can be used as a catalyst to synthesize:Glycofused tricyclic derivatives, which are used in the development of amyloid β-peptide diagnostic tools.Cyclohexene carbaldehyde derivatives by reacting benzoylnitromethane with aliphatic enals.

General Description

(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol trimethylsilyl ether is a diarylprolinol silyl ether organocatalyst.

InChI:InChI=1/C19H23NOSi/c1-22(2)20-15-9-14-18(20)19(21-22,16-10-5-3-6-11-16)17-12-7-4-8-13-17/h3-8,10-13,18H,9,14-15H2,1-2H3/t18-/m1/s1

Synthetic route

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride (837-95-6) → C27H29F3N2O5SSi

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	95%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((4-nitrophenyl)sulfonyl)pyrrolidine

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	94%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 4-chlorosulfonyl-3-nitrobenzoic acid methyl ester (162010-78-8) → C28H32N2O7SSi

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	93%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((2-nitrophenyl)sulfonyl)pyrrolidine

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	92%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 3-nitrobenzenesulphonyl chloride (121-51-7) → (R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-1-((3-nitrophenyl)sulfonyl)pyrrolidine

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	91%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 4-methoxy-2-nitrobenzenesulfonyl chloride (18092-54-1) → C27H32N2O6SSi

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	90%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 4-chloro-2-nitrobenzenesulfonyl chloride (4533-96-4) → C26H29ClN2O5SSi

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	88%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-4-methyl-2-(2-nitrovinyl)phenol (264224-82-0) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-2,6-dimethyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-98-4)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-methyl-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	87%

4-fluoro-2-nitrobenzene-1-sulfonyl chloride (568586-10-7) + (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) → C26H29FN2O5SSi

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	85%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + trans-4-bromo-2-(2-nitrovinyl)phenol (61131-72-4) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-6-bromo-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-96-2)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; trans-4-bromo-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	83%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 4-fluoro-2-((E)-2-nitrovinyl)phenol (1308249-79-7) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-6-fluoro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-94-0)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 4-fluoro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-4-chloro-2-(2-nitroethenyl)phenol (61131-68-8) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-6-chloro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-95-1)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-chloro-2-(2-nitroethenyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2,4-chloro-2-((E)-2-nitrovinyl)phenol (1310493-82-3) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-6,8-dichloro-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-97-3)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2,4-chloro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-4-methoxy-2-(2-nitrovinyl)phenol (35467-98-2) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-6-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-99-5)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-4-methoxy-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	82%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + 2-((1E)-2-nitrovinyl)-4-nitrophenol → (-)-(E)-ethyl 3-((2S,3R,4R)-8-hydroxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631166-02-3)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; acetaldehyde; 2-((1E)-2-nitrovinyl)-4-nitrophenol In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	80%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2-[(E)-2-nitrovinyl]phenol (3156-43-2) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631165-93-9)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h; Reagent/catalyst; Concentration; Temperature; Solvent;	80%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-5-methoxy-2-(2-nitrovinyl)phenol (96853-34-8) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-7-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631166-00-1)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-5-methoxy-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	80%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2-[(E)-2-nitrovinyl]phenol (3156-43-2) + acetaldehyde (75-07-0) → (-)-(2S,3R,4R)-2-methyl-4-(nitromethyl)chroman-3-carbaldehyde (1631165-92-8)

Conditions	Yield
In chloroform at -40 - -5℃; for 3.25h;	80%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-2-methoxy-6-(2-nitrovinyl)phenol (1986-06-7, 141849-32-3) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-8-methoxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631166-01-2)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-2-methoxy-6-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	75%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + (E)-3-(2-nitrovinyl)benzene-1,2-diol (1308250-94-3) + acetaldehyde (75-07-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (-)-(E)-ethyl 3-((2S,3R,4R)-8-hydroxy-2-methyl-4-(nitromethyl)chroman-3-yl)acrylate (1631166-02-3)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-3-(2-nitrovinyl)benzene-1,2-diol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl (triphenylphosphoranylidene)acetate In chloroform at 20℃; for 2h;	75%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 2-[(E)-2-nitrovinyl]phenol (3156-43-2) + acetaldehyde (75-07-0) → (-)-((2S,3S,4R)-2-methyl-4-(nitromethyl)chroman-3-yl)methanol (1631165-85-9)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; for 3.25h; Stage #2: With methanol; sodium tetrahydroborate In chloroform at 0℃; for 1h;	75%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + ethyl 2-diethoxyphosphinoylacrylate (20345-61-3) + 2-[(E)-2-nitrovinyl]phenol (3156-43-2) + acetaldehyde (75-07-0) → (-)-(6S,6aR,10S,10aR)-ethyl 6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate (1631166-04-5)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2-[(E)-2-nitrovinyl]phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	75%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + isovaleraldehyde (590-86-3) → C25H35NOSi

Conditions	Yield
In dimethylsulfoxide-d6	75%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + ethyl 2-diethoxyphosphinoylacrylate (20345-61-3) + (E)-3-(2-nitrovinyl)benzene-1,2-diol (1308250-94-3) + acetaldehyde (75-07-0) → (-)-(6S,6aR,10S,10aR)-ethyl 4-hydroxy-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate (1631166-07-8)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; (E)-3-(2-nitrovinyl)benzene-1,2-diol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	72%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + ethyl 2-diethoxyphosphinoylacrylate (20345-61-3) + 2,4-chloro-2-((E)-2-nitrovinyl)phenol (1310493-82-3) + acetaldehyde (75-07-0) → (-)-(6S,6aR,10S,10aR)-ethyl 2,4-dichloro-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate (1631166-06-7)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; 2,4-chloro-2-((E)-2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	70%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + ethyl 2-diethoxyphosphinoylacrylate (20345-61-3) + trans-4-bromo-2-(2-nitrovinyl)phenol (61131-72-4) + acetaldehyde (75-07-0) → (-)-(6S,6aR,10S,10aR)-ethyl 2-bromo-6-methyl-10-nitro-6a,9,10,10a-tetrahydro-6H-benzo[c]chromene-8-carboxylate (1631166-05-6)

Conditions	Yield
Stage #1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; trans-4-bromo-2-(2-nitrovinyl)phenol; acetaldehyde In chloroform at -40 - -5℃; Wittig-Horner Reaction; Stage #2: ethyl 2-diethoxyphosphinoylacrylate With caesium carbonate In dichloromethane at 0℃; for 6h; Inert atmosphere; Stage #3: With ethanol In dichloromethane at 0 - 20℃; for 2h;	67%

(R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 1-nitroethanol (39221-06-2) + 4-methoxy-trans-cinnamaldehyde (24680-50-0, 71277-11-7, 1963-36-6) → (4R,5R)-4-(2-methoxyphenyl)-5-nitrotetrahydro-2H-pyran-2-ol

Conditions	Yield
With benzoic acid In methanol at 40℃; for 10h; Inert atmosphere;	51%

nitrostyrene (5153-67-3) + (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + acetaldehyde (75-07-0) → (3R)-4-nitro-3-phenylbutanal (934269-53-1) + C14H15NO3

Conditions	Yield
In chloroform at -40 - -5℃; for 96h;	A 25% B 25%

nitrostyrene (5153-67-3) + (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) + 5-formy-1,3,6-trimethyluracil (23941-84-6) → (5R,6R,7R)-5-((R)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-1,3-dimethyl-6-nitro-7-phenyl-5,6,7,8-tetrahydroquinazoline-2,4(1H,3H)-dione

Conditions	Yield
In dichloromethane at 25℃; for 24h; Inert atmosphere;	18%

nitrostyrene (5153-67-3) + (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine (943757-71-9) → C8H7NO2*C20H27NOSi

Conditions	Yield
In methanol for 0.166667h;

Downstream Products

• 934269-53-1 (3R)-4-nitro-3-phenylbutanal