(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine supplier

Name
(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol
EINECS 606-992-7
CAS No. 22348-32-9
Article Data55
CAS DataBase
Density 1.128 g/cm³
Solubility
Melting Point 77-80 °C
Formula C₁₇H₁₉NO
Boiling Point 411.3 °C at 760 mmHg
Molecular Weight 253.344
Flash Point 133.3 °C
Transport Information
Appearance white to faintly yellow crystalline powder
Safety 133.3 °C
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Pyrrolidinemethanol,a,a-diphenyl-, (R)- (8CI);(+)-2-(Diphenylhydroxymethyl)pyrrolidine;(+)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-2-(diphenylhydroxymethylpyrrolidine);(R)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-a,a-Diphenylprolinol;a,a-Diphenyl-D-prolinol;α,α-Diphenyl-D-prolinol;
PSA 32.26000
LogP 3.00330

Synthetic route

: 137496-68-5
2-(hydroxy(diphenyl)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
With sodium hydroxide In ethanol for 2.5h; Reflux;	100%
With sodium hydroxide In ethanol at 79℃; for 4h;	90%

: (R)-1-tert-butyl-(λ1-oxidanyl)-(λ3-sulfanyl)-2-((methoxymethoxy)diphenylmethyl)pyrrolidine

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Stage #1: (R)-1-tert-butyl-(λ1-oxidanyl)-(λ3-sulfanyl)-2-((methoxymethoxy)diphenylmethyl)pyrrolidine With hydrogenchloride In methanol at 0 - 70℃; for 4h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; methanol at 20℃; for 6h;	91%

: 63401-04-7
diphenyl(pyrrolidin-2-yl)methanol

: 22348-32-9
(R)-α,α-diphenylprolinol

: 90971-03-2
(R)-Tetrahydro-1H,3H-pyrrolo<1,2-c>oxazole-1,3-dione

: phenylmagnesium chloride

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
In tetrahydrofuran Yield given;

: 63401-04-7
diphenyl(pyrrolidin-2-yl)methanol

A: 22348-32-9, 63401-04-7, 112022-88-5, 112068-01-6
(S)-diphenylprolinol

B: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Stage #1: diphenyl(pyrrolidin-2-yl)methanol With (R)-1,1'-Bi-2-naphthol; boric acid In acetonitrile Heating; Stage #2: With hydrogenchloride In diethyl ether; water Further stages.;

: 119-61-9
benzophenone

zinc dust: zinc dust

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) s-BuLi, (-)-sparteine, 3.) AcOH 2: 90 percent / NaOH / ethanol / 4 h / 79 °C View Scheme

: phenylmagnesium chloride

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / tetrahydrofuran / 24 h / 23 °C 2: 77 percent / BH3 / tetrahydrofuran View Scheme

: 4931-66-2, 54571-66-3, 64700-65-8
methyl 5-oxopyrrolidine-2-carboxylate

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / tetrahydrofuran / 24 h / 23 °C 2: 77 percent / BH3 / tetrahydrofuran View Scheme

: 149-87-1
Pyroglutamic acid

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / 5 molpercent hydrogen chloride (from acetyl chloride) / 24 h / 23 °C 2: 70 percent / tetrahydrofuran / 24 h / 23 °C 3: 77 percent / BH3 / tetrahydrofuran View Scheme

: 21901-76-8
5-(hydroxy-diphenyl-methyl)-pyrrolidin-2-one

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / BH3 / tetrahydrofuran View Scheme

: 356790-44-8
C24H25NO

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 18h; Inert atmosphere;

: C20H23NO3

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 48h; Reflux;

: 100-59-4
phenylmagnesium chloride

: 73323-65-6
1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Stage #1: phenylmagnesium chloride; 1-(tert-butyl) 2-methyl (R)-pyrrolidine-1,2-dicarboxylate In tetrahydrofuran at 10 - 60℃; Industrial scale; Stage #2: With hydrogenchloride In water at 45℃; for 9h; Industrial scale; Stage #3: With sodium hydroxide Industrial scale;	n/a

: 223930-75-4
((methoxymethoxy)methylene)dibenzene

: 22348-32-9
(R)-α,α-diphenylprolinol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: hydrogenchloride / methanol / 4 h / 0 - 70 °C 2.2: 6 h / 20 °C View Scheme

: 1633-82-5
3-chloro-n-propanesulfonyl chloride

: 22348-32-9
(R)-α,α-diphenylprolinol

: 1370293-21-2
(R)-(1-(3-chloropropylsulfonyl)pyrrolidin-2-yl)diphenylmethanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%

: 5419-55-6
Triisopropyl borate

: 22348-32-9
(R)-α,α-diphenylprolinol

: 107-21-1
ethylene glycol

: (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions

Conditions	Yield
In toluene at 80℃; for 1h; Inert atmosphere;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere; Reflux;	100%
Stage #1: Triisopropyl borate; ethylene glycol In toluene Inert atmosphere; Reflux; Stage #2: (R)-α,α-diphenylprolinol In toluene at 80℃; for 1h; Inert atmosphere;	90%

...Expand

: 47127-05-9
phenylbis(diisopropylamino)borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: (S)-tetrahydro-1,3,3-triphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazoborolidine

Conditions

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	96%

: 151293-62-8
butylbis(diisopropylamino)borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole

Conditions

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	95%

: 144-79-6
chloromethyldiphenylsilane

: 22348-32-9
(R)-α,α-diphenylprolinol

: (R)-2-(((methyldiphenylsilyl)oxy)diphenylmethyl)pyrrolidine

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	93%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 157952-85-7
2-iodo-4,4-dimethyl-cyclohex-2-enone

: (S)-2-iodo-4,4-dimethyl-2-cyclohexen-1-ol

Conditions

Conditions	Yield
Stage #1: (R)-α,α-diphenylprolinol With Trimethyl borate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 2-iodo-4,4-dimethyl-cyclohex-2-enone With N,N-diethylaniline borane In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	92%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 99701-64-1
N-((2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)-methyl)-tetrahydro-2H-pyran-2-yl)-2,2,2-trichloroacetamide

: 1158857-93-2
C52H54N2O7

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	90%
With caesium carbonate In N,N-dimethyl-formamide at 25℃; Schlenk technique; Inert atmosphere;	90%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 107-21-1
ethylene glycol

: (R)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine

Conditions

Conditions	Yield
With Triisopropyl borate	90%
Stage #1: ethylene glycol With Triisopropyl borate In toluene at 105℃; Inert atmosphere; Stage #2: (R)-α,α-diphenylprolinol In toluene for 1h; Inert atmosphere;

: 151293-60-6
methylbis(diisopropylamino)borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In tetrahydrofuran; toluene reflux for 30 min; solvents are removed;	89%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: (R)-(1-((2-nitrophenyl)sulfonyl)pyrrolidin-2-yl)diphenylmethanol

Conditions

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

: 13061-96-6
dihydroxy-methyl-borane

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-81-8
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In n-heptane at 40℃; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;	83%

: 7703-74-4
2,6-bis-(bromomethyl)pyridine

: 22348-32-9
(R)-α,α-diphenylprolinol

: 1310579-92-0
(2R,2'R)-1,1'-(pyridine-2,6-diylbis(methylene))bis[2-(diphenylmethanol)pyrrolidine]

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol at 20℃; for 8h;	78%

: 31106-82-8
2-(bromomethyl)pyridine hydrobromide

: 22348-32-9
(R)-α,α-diphenylprolinol

: 132902-42-2
(R)-2-(diphenylmethanol)-1-(pyridin-2-ylmethyl)pyrrolidine

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In ethanol at 20℃; for 10h;	76%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 2950-83-6
4-(2,4-dioxo-1,2,3,4-tetrahydro-1-pyrimidinyl)butanoic acid

: 1204659-22-2
(R)-1-(4-(2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)-4-oxobutyl)pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	66%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: (S)-2-[(R)-2-(Hydroxy-diphenyl-methyl)-pyrrolidine-1-carbonyl]-pyrrolidine-1-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In chloroform for 12h;	65%

: 22348-32-9
(R)-α,α-diphenylprolinol

: 4998-15-6
4-chlorophenylglyoxal

: 1620212-19-2
1-(4-chlorophenyl)-2-[2-(diphenylmethylene)pyrrolidin-1-yl]ethane-1,2-dione

Conditions

Conditions	Yield
With gold(III) tribromide In dichloromethane at 60℃; for 12h; Schlenk technique;	62%

: 69739-34-0
t-butyldimethylsiyl triflate

: 22348-32-9
(R)-α,α-diphenylprolinol

: 1236033-34-3
(R)-2-(((tert-butyldimethylsilyl)oxy)diphenylmethyl)pyrrolidine

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 22℃; for 12h; Inert atmosphere;	56%

: 50777-76-9
(2-formylphenyl)(diphenyl)phosphine

: 22348-32-9
(R)-α,α-diphenylprolinol

: (2R,5R)-1-aza-2-(2-diphenylphosphino)phenyl-3-oxa-4,4-diphenylbicyclo[3.3.0]octane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 24h; Cycloaddition; Heating;	54%

: 1252606-18-0
(1R,4R,7R)-7-isopropyl-5-methylbicyclo[2.2.2]octane-2,5-diene-2-carboxylic acid

: 22348-32-9
(R)-α,α-diphenylprolinol

: ((R)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl)((1R,4R,7R)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-dien-2-yl)methanone

Conditions

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃; for 16h; Inert atmosphere; Schlenk technique;	31%

: 823-96-1
Trimethylboroxine

: 22348-32-9
(R)-α,α-diphenylprolinol

: 112022-83-0
(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

Conditions

Conditions	Yield
In toluene Heating;
With borane In toluene at 20 - 150℃; for 4.5h;
In toluene at 20℃; for 0.5h;

: 121-43-7
Trimethyl borate

: 22348-32-9
(R)-α,α-diphenylprolinol

: (R)-2-methoxy-CBS-oxazaborolidine

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 45℃; for 10h;
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
In tetrahydrofuran
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #1: Trimethyl borate; (R)-α,α-diphenylprolinol In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With dimethylsulfide borane complex In tetrahydrofuran Inert atmosphere;

: 22348-32-9
(R)-α,α-diphenylprolinol

: (R)-(+)-2-methyl-CBS-oxazaborolidine

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 45℃; for 10h;
With dimethylsulfide borane complex In tetrahydrofuran; toluene at 20℃; for 1h; Inert atmosphere;
With borane-THF

: 7294-50-0
tri-o-tolylboroxine

: 22348-32-9
(R)-α,α-diphenylprolinol

: 82113-65-3
bis(trifluoromethanesulfonyl)amide

: (R)-(+)-3,3-diphenyl-1-o-tolyl-tetrahydropyrrolo-(1,2-c)(1,3,2)oxazaborole-1,1,1-trifluoro-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

Conditions

Conditions	Yield
Stage #1: tri-o-tolylboroxine; (R)-α,α-diphenylprolinol With 4A MS In toluene for 3h; Heating; Stage #2: bis(trifluoromethanesulfonyl)amide In dichloromethane at -25℃; for 0.25h;

...Expand

: tri-o-tolylboroxine

: 22348-32-9
(R)-α,α-diphenylprolinol

: 82113-65-3
bis(trifluoromethanesulfonyl)amide

: (R)-(+)-3,3-diphenyl-1-o-tolyl-tetrahydropyrrolo-(1,2-c)(1,3,2)oxazaborole-1,1,1-trifluoro-N-((trifluoromethyl)-sulfonyl)methanesulfonamide

Conditions

Conditions	Yield
Stage #1: tri-o-tolylboroxine; (R)-α,α-diphenylprolinol In toluene at 145℃; for 3h; Stage #2: bis(trifluoromethanesulfonyl)amide In toluene at -20℃; for 0.333333h;

...Expand

: 7294-50-0
tri-o-tolylboroxine

: 22348-32-9
(R)-α,α-diphenylprolinol

: (R)-2-(o-methyl)phenyl-CBS-oxazaborolidine

Conditions

Conditions	Yield
In toluene Heating;
With 4 A molecular sieve In toluene Heating;
In toluene for 20h; Reflux;

(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine Chemical Properties

Synonyms: ALPHA,ALPHA-DIPHENYL-D-PROLINOL;2-PYRROLIDINEMETHANOL, A,A-DIPHENYL-;A,A-DIPHENYL-D-PROLINOL;(R)-(+)-2-(DIPHENYLHYDROXYMETHYL)PYRROLIDINER(+)-A,A-DIPHENYLPROLINOL;(R)-1-DIPHENYL-PROLINOL;(R)-(+)-2-(DIPHENYLHYDROXYMETHYL)-PYRROLIDIN;;(R)-2-(DIPHENYLHYDROXYMETHYL)PYRROLIDINE;
(R)-α, α-Diphenyl-2-pyrrolidinemethanol is the chemical compound with the formula C₁₇H₁₉NO.Its molecular weight is 253.34.
Molecular Structure:
Melting point:77-80 °C
alpha:59 ^o(589nm, c=3, MeOH 25 ^oC)
refractive index:58 °(C=2, MeOH)

(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine Safety Profile

(R)-α, α-Diphenyl-2-pyrrolidinemethanol's Hazard Codes: Xi
(R)-α, α-Diphenyl-2-pyrrolidinemethanol's Risk Statements:
36/37/38:Irritating to eyes, respiratory system and skin
(R)-α, α-Diphenyl-2-pyrrolidinemethanol's Safety Statements:
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
37/39:Wear suitable gloves and eye/face protection
WGK Germany:3
F:F 10 Keep under argon;F 34 Sensitive to CO₂.

Product Name

(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol

Synthetic route

(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine Chemical Properties

(R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine Safety Profile

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