134002-25-8

Basic information

• Product Name: 3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine
• Synonyms: (S)-ALPHA,ALPHA-DIPHENYL-3-PYRROLLIDINEACETAMIDE;3-(S)-(1-CARBAMOYL-1,1-DIPHENYLMETHYL)PYRROLIDINE;(S)-Alpha,Alphal-Diphenyl-3-Pyrrolidineacetamide-L-tartrate(Darifenacin);(S)-alpha,alphal-Diphenyl-3-pyrrolidineacetamide;(3S)-diphenyl-3-Pyrrolidineacetamide;(s),-L,L-dipenyl-3-pyrrolidine acetamide L-tartaric acid salt;3-(S)-(1-Carbamoyl-1;(S)-3-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine
• CAS NO: 134002-25-8
• Molecular Formula: C₁₈H₂₀N₂O
• Molecular Weight: 280.36
• EINECS: 1533716-785-6
• Product Categories: Pharmaceutical material and intermeidates;APIs Intermediate;Benzenes
• Mol File: 134002-25-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 114-118 °C
• Boiling Point: 488.5 °C at 760 mmHg
• Flash Point: 249.2 °C
• Appearance: /
• Density: 1.147 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C(protect from light)
• PKA: 15.70±0.50(Predicted)
• CAS DataBase Reference: 3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine(134002-25-8)
• EPA Substance Registry System: 3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine(134002-25-8)

Safety Data

• Hazardous Substances Data: 134002-25-8(Hazardous Substances Data)

Usage

General Description

3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine is a chemical compound with a complex structure and a long name. It is a pyrrolidine derivative with a carbamoyl group and a 1,1-diphenylmethyl group attached to the nitrogen atom of the pyrrolidine ring. 3-(S)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine has potential applications in medicinal chemistry and drug development, as pyrrolidine derivatives are known to exhibit a variety of biological activities. The presence of the carbamoyl group suggests that this compound may have interactions with enzymes or receptors in the body, making it a potentially interesting molecule for further research and development. The specific stereochemistry indicated by the (S) in the name further adds to the complexity and potential specificity of this compound's biological activity.

InChI:InChI=1/C18H20N2O/c19-17(21)18(16-11-12-20-13-16,14-7-3-1-4-8-14)15-9-5-2-6-10-15/h1-10,16,20H,11-13H2,(H2,19,21)

Synthetic route

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile (133099-11-3) → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
With sulfuric acid In water at 85 - 90℃; for 14h;	100%
With sulfuric acid at 85 - 90℃; for 12h;	76%
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile With water; sulfuric acid at 90℃; for 24h; Stage #2: With sodium hydroxide In water pH=12;	58%

3-(R,S)-(1-carbamoyl-1,1-diphenyl-methyl)pyrrolidine → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
Stage #1: 3-(R,S)-(1-carbamoyl-1,1-diphenyl-methyl)pyrrolidine With tartaric acid In ethanol for 10 - 20h; Stage #2: In methanol at 70℃; for 15h;	58%

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
With sodium hydroxide In methanol; water	58%
With sodium hydroxide; water In dichloromethane pH=12;
With sodium hydroxide In water; ethyl acetate Product distribution / selectivity;
With sodium hydroxide In water at 25 - 60℃; for 0.333333h; pH=12 - 14; Product distribution / selectivity;
With sodium hydroxide In water; toluene pH=12; Product distribution / selectivity;

3-(S)-(+)-(1-cyano-1,1-diphenylmethyl)pyrrolidine hydrobromide → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 25 - 30℃; for 0.0833333h;

(3R)-pyrrolidinol (40499-83-0, 83220-72-8, 100243-39-8, 2799-21-5) → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
With sulfuric acid; sodium hydroxide In dichloromethane; water at 50 - 105℃; pH=10 - 12;

(S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile (1189753-52-3) → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
Stage #1: (S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile With sulfuric acid at 110℃; Stage #2: With sodium hydroxide In water at 30℃; pH=10 - 12;
Multi-step reaction with 2 steps 1: hydrogenchloride / methanol / 7 h / 20 - 30 °C 2: sulfuric acid / 12 h / 85 - 90 °C View Scheme

(S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile (133099-09-9) → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen bromide / water; phenol / 4 h / Heating / reflux 2.1: sulfuric acid / 10 h / 95 - 100 °C 2.2: 25 - 30 °C View Scheme

Diphenylacetonitrile (86-29-3) → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 2 h 1.2: 5 h / 95 - 100 °C 2.1: hydrogen bromide / water; phenol / 4 h / Heating / reflux 3.1: sulfuric acid / 10 h / 95 - 100 °C 3.2: 25 - 30 °C View Scheme

C2H2O4*C18H18N2 → 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 0.25 h / 50 - 60 °C / pH 12 2.1: sulfuric acid / 10 h / 95 - 100 °C 2.2: 25 - 30 °C View Scheme

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + N-(5-bromopentyl)phthalimide (954-81-4) → 2-{(S)-1-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pentyl]pyrrolidin-3-yl}-2,2-diphenylacetamide (864766-81-4)

Conditions	Yield
With triethylamine In acetonitrile at 55℃; for 8h;	100%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + formaldehyd (50-00-0) → 2-((S)-1-methylpyrrolidin-3-yl)-2,2-diphenylacetamide (1050646-81-5)

Conditions	Yield
With hydrogen In methanol; water	96.4%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 8,8-dimethoxyoctanal (148315-77-9) → 2-[(S)-1-(8-Oxooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide (808757-08-6)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 8,8-dimethoxyoctanal In dichloromethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 14h;	93%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 8-(N-Benzyl-N-methylamino)octan-1-ol (808757-04-2) → 2-[(S)-1-(8-N-benzyl-N-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide (808757-06-4)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 8-(N-Benzyl-N-methylamino)octan-1-ol With N-ethyl-N,N-diisopropylamine In acetonitrile at 45 - 50℃; for 20h; Stage #2: With acetic anhydride In acetonitrile	90%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + toluenesulfonic acid 8-(N-benzyl-N-methylamino)octan-1-yl ester (808757-07-5) → 2-[(S)-1-(8-N-benzyl-N-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide (808757-06-4)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; toluenesulfonic acid 8-(N-benzyl-N-methylamino)octan-1-yl ester With N-ethyl-N,N-diisopropylamine In acetonitrile at 45 - 50℃; for 20h; Stage #2: With acetic anhydride In acetonitrile at 20℃; for 2h; Stage #3: With ammonium hydroxide In water pH=12;	90%

2,3-dihydro-5-(2-bromoethyl)benzofuran (127264-14-6) + 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) → (S)-darifenacin hydrobromide (133099-07-7)

Conditions	Yield
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Heating / reflux; Stage #2: With hydrogen bromide In water; butanone	84.92%
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In acetonitrile at 70 - 75℃; for 2h; Stage #2: With hydrogen bromide In water; acetone at 0 - 25℃; Product distribution / selectivity;
With potassium carbonate In acetonitrile

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 5-hexynal (29329-03-1) → (S)-3-(1-carbamoyl-1,1-diphenylmethyl)-1-(hex-5-yn-1-yl)pyrrolidine (690998-86-8)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 5-hexynal With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 8h; Stage #2: With hydrogenchloride In dichloromethane at 20℃; for 1h;	83%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 8h;	83%
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 5-hexynal With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃; for 1h; Stage #3: With sodium hydroxide In dichloromethane; water pH=5;	83%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + tartaric acid (87-69-4) → (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

Conditions	Yield
In ethanol for 1h;	80%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + toluene-4-sulfonic acid 8-(N-tert-butoxycarbonyl-N-methylamino)octyl ester (1056998-28-7) → 2-{(S)-1-[8-(N-tert-butoxycarbonyl-N-methylamino)octyl]-pyrrolidin-3-yl}-2,2-diphenylacetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60 - 65℃; for 5 - 7h;	77%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 8-(N-Benzyl-N-methylamino)octanal → 2-[(S)-1-(8-N-benzyl-N-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide (808757-06-4)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 8-(N-Benzyl-N-methylamino)octanal In dichloromethane at 0℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 20℃; for 4h;	75%
With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 20℃; for 4h;	75%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 7,7-dimethoxyheptanal (60090-77-9) → (S)-3-(1-carbamoyl-1,1-diphenylmethyl)-1-(7,7-dimethoxyhept-1-yl)pyrrolidine (690999-17-8)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 7,7-dimethoxyheptanal In dichloromethane at 0 - 5℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 5 - 20℃; for 6.5h; Stage #3: With potassium carbonate In dichloromethane; water at 20℃; for 1h;	72%
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 7,7-dimethoxyheptanal In dichloromethane at 0 - 5℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 5℃; for 6.5h; Product distribution / selectivity;	72%
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 7,7-dimethoxyheptanal In dichloromethane at 0 - 5℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 5 - 20℃; for 6.5h;

2-(2,3-dihydrobenzofuran-5-yl)ethylchloride (943034-50-2) + 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) → (S)-darifenacin hydrobromide (133099-07-7)

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With sodium hydroxide; water In ethyl acetate at 25 - 35℃; for 0.25h; Stage #2: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride With triethylamine at 95℃; for 15h; Stage #3: With hydrogen bromide In water; acetone for 1h; Product distribution / selectivity;	70%
Stage #1: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In water at 101 - 103℃; for 2 - 5h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity;

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → (S)-2-(1-(2-((tert-butyldimethylsilyl)oxy)ethyl)pyrrolidin-3-yl)-2,2-diphenylacetamide

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h; Inert atmosphere;	70%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 9-bromononan-1-ol (55362-80-6) → 2-[(S)-1-(9-hydroxynonyl)pyrrolidin-3-yl]-2,2-diphenylacetamide

Conditions	Yield
With triethylamine In acetonitrile at 20 - 50℃; for 24h;	62%
With triethylamine In acetonitrile at 50℃;	62%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 4-[N-(7-bromo-4-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (690999-02-1) + 4-methyl-2-pentanone (108-10-1) → 4-{N-[7-(3-(S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidin-1-yl)-4-oxahept-1-yl]-N-(isopropyl)amino}-1-benzylpiperidine

Conditions	Yield
With sodium carbonate; potassium iodide In DMF (N,N-dimethyl-formamide) at 110℃; for 21h;	56%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 7-bromoheptyl alcohol (10160-24-4) → (S)-3-(1-carbamoyl-1,1-diphenylmethyl)-1-(7-hydroxyhept-1-yl)pyrrolidine (690998-84-6)

Conditions	Yield
With triethylamine In acetonitrile at 40 - 50℃; for 9h;	56%
With triethylamine In acetonitrile at 40 - 50℃; for 9h;	56%
With triethylamine In acetonitrile at 40 - 50℃; for 9h;	56%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 4-[N-(7-bromo-4-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (690999-02-1) → 4-{N-[7-(3-(S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidin-1-yl)-4-oxahept-1-yl]-N-(isopropyl)amino}-1-benzylpiperidine

Conditions	Yield
With sodium carbonate; potassium iodide In DMF (N,N-dimethyl-formamide); 4-methyl-2-pentanone at 110℃; for 21h;	56%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 8-bromooctanol (50816-19-8) → 2-[(S)-1-(8-Hydroxyoctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide

Conditions	Yield
With triethylamine In acetonitrile at 40 - 55℃; for 16h;	44%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 4-[N-(7-bromo-3-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (690999-08-7) → 4-{N-[7-(3-(S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidin-1-yl)-3-oxahept-1-yl]-N-(isopropyl)amino}-1-benzylpiperidine

Conditions	Yield
With triethylamine In acetonitrile for 24h; Heating / reflux;	32%
With triethylamine In acetonitrile for 24h; Heating / reflux;	32%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 4-[N-(7-bromo-5-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (1382621-66-0) → 4-{N-[7-(3-(S)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidin-1-yl)-5-oxahept-1-yl]-N-(isopropyl)amino}-1-benzylpiperidine (690999-10-1)

Conditions	Yield
With triethylamine In acetonitrile for 24h; Heating / reflux;	29%
With triethylamine In acetonitrile for 24h; Heating / reflux;	29%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + L-Tartaric acid (87-69-4) → (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate

Conditions	Yield
In ethanol for 2.16667h; Heating; Reflux;	16.95%
In ethanol for 10 - 20h;
In ethanol
In toluene at 25 - 60℃; for 12.75h;
In water at 50 - 60℃;

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 1,8-dibromooctane (4549-32-0) → 2-[(S)-1-(8-bromoooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); acetone at 40℃; for 5h;	15%

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) → 2-[(S)-1-(3-{4-[2-(Benzylmethylamino)-ethyl]phenyl}propyl)pyrrolidin-3-yl]-2,2-diphenylacetamide

Conditions	Yield
Stage #1: 3-{4-[2-(Benzylmethylamino)ethyl]phenyl}propionitrile With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 3h; Stage #2: With methanol In dichloromethane; toluene for 0.166667h; Stage #3: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With hydrogenchloride; sodium hydroxide; sodium tris(acetoxy)borohydride more than 3 stages;	10%

2,3-dihydro-5-(2-bromoethyl)benzofuran (127264-14-6) + 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) → darifenacin (133099-04-4)

Conditions	Yield
With potassium carbonate In acetonitrile for 2h; Heating / reflux;	9%
With potassium phosphate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium carbonate In water; toluene at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium phosphate In cyclohexane; water at 20 - 90℃; for 3.5h; Product distribution / selectivity;
With potassium hydroxide In acetonitrile at 40 - 50℃; for 18h; Product distribution / selectivity;

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 1,8-dibromooctane (4549-32-0) + trifluoroacetic acid (76-05-1) → 2-[(S)-1-(8-dimethylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide bis(trifluoroacetate) salt

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 1,8-dibromooctane; dimethyl amine In chloroform at 50℃; for 60h; Stage #2: trifluoroacetic acid

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (134002-25-8) + 8,8-dimethoxyoctanal (148315-77-9) → C28H40N2O3

Conditions	Yield
Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide; 8,8-dimethoxyoctanal In dichloromethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 14h; Stage #3: With sodium hydrogencarbonate In dichloromethane; water for 0.5h;

Upstream product

• 133099-11-3 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile 
• 103887-32-7 3-(R,S)-(1-carbamoyl-1,1-diphenyl-methyl)pyrrolidine 
• 86-29-3 Diphenylacetonitrile 
• 133099-09-9 (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile 
• 1189753-52-3 (S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile 
• 40499-83-0 (3R)-pyrrolidinol 
• 134002-26-9 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate 

Downstream Products

• 690998-84-6 (S)-3-(1-carbamoyl-1,1-diphenylmethyl)-1-(7-hydroxyhept-1-yl)pyrrolidine 
• 864766-81-4 2-{(S)-1-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pentyl]pyrrolidin-3-yl}-2,2-diphenylacetamide 
• 1050646-79-1 2-[(S)-1-(3-phenoxypropyl)pyrrolidin-3-yl]-2,2-diphenylacetamide 
• 133099-07-7 (S)-darifenacin hydrobromide 
• 134002-26-9 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate 
• 586346-94-3 darifenacin hydrochloride 
• 690999-15-6 TD-6301 
• 133034-07-8 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl]-pyrrolidine 
• 133034-08-9 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl]-pyrrolidine hydrochloride 
• 808757-06-4 2-[(S)-1-(8-N-benzyl-N-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide 
• 808757-08-6 2-[(S)-1-(8-Oxooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide 

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Darifenacin is a potent and competitive M3 selective receptor antagonist (M3SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).

IMPROVED PROCESS FOR PRODUCING DARIFENACIN

The present invention discloses an improved process for producing darifenacin, the process comprising decarboxylating (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid followed by in situ tosylation to give l-tosyl-3-(R)-(-)-hydroxypyrrolidine, tosylating the l-tosyl-3-(R)-(-)-hydroxypyrrolidine with methyl-p-toluenesuolphonate to give l-tosyl-3- (S)-(-)-tosyloxy pyrrolidine, reacting l-tosyl-3-(S)-(-)-tosyloxy pyrrolidine with diphenyl acetonitrile in presence of a base to give 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine, de-protecting 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine in the presence of phenol in acidic medium to give 3-(S)-(+)-(l-cyano- 1,1-diphenylmethyl) pyrrolidine, hydrolyzing 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl) pyrrolidine followed by salt formation to obtain 3-(S)-(+)-(l-carbamoyl-l,l- diphenylmethyl)pyrrolidine.L-(+)-tartrate, condensing 3-(S)-(+)-( 1 -carbamoyl- 1,1- diphenylmethyl)pyrrolidine-L(+)-tartrate with 5-(2-bromoethyl)-2,3-dihydrobenzofuran employing a base in a solvent to give darifenacin.

SUBSTITUTED PYRROLIDINES

Disclosed herein are substituted pyrrolidine-based muscarinic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.