133034-00-1

Basic information

• Product Name: 1-(P-TOSYL)-(R)-(-)-3-PYRROLIDINOL 98
• Synonyms: 1-(P-TOSYL)-(R)-(-)-3-PYRROLIDINOL 98;R-1-(p-Tosyl)-3-pyrrolidinol;S-1-Methylpyrrolidin-3-aMine.2HCl;(R)-1-tosylpyrrolidin-3-ol;1-Tosyl-(3S)-hydroxy pyrrolidine;(R)-1-(p-Tosyl)-3-pyrrolidinol,99%e.e.
• CAS NO: 133034-00-1
• Molecular Formula: C₁₁H₁₅NO₃S
• Molecular Weight: 241.309
• Mol File: 133034-00-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 61-65 °C(lit.)
• Boiling Point: 406.8°Cat760mmHg
• Flash Point: 199.9°C
• Appearance: /
• Density: 1.338g/cm³
• Vapor Pressure: 2.38E-07mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 1-(P-TOSYL)-(R)-(-)-3-PYRROLIDINOL 98(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(P-TOSYL)-(R)-(-)-3-PYRROLIDINOL 98(133034-00-1)
• EPA Substance Registry System: 1-(P-TOSYL)-(R)-(-)-3-PYRROLIDINOL 98(133034-00-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 133034-00-1(Hazardous Substances Data)

Usage

Uses

(3R)-1-[(4-Methylphenyl)sulfonyl]-3-pyrrolidinol is a useful building block in organic synthesis.

InChI:InChI=1/C11H15NO3S/c1-9-2-4-11(5-3-9)16(14,15)12-7-6-10(13)8-12/h2-5,10,13H,6-8H2,1H3/t10-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 104706-47-0 (R)-3-hydroxypyrrolidine hydrochloride 
• 40499-83-0 (3R)-pyrrolidinol 

Downstream Products

• 133099-09-9 (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile 
• 1307881-27-1 (R)-3-sulfamoyloxy-N-(toluene-4-sulfonyl)pyrrolidine 

Relevant articles and documents

Correction to: Rhodium/yanphos-catalyzed asymmetric interrupted intramolecular hydroaminomethylation of trans-1,2-disubstituted alkenes (J. Am. Chem. Soc. (2016) 138 (9017?9020) (DOI: 10.1021/jacs.6b03596)

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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.

Muscarinic receptor antagonists

Muscarinic receptor antagonists of formula (I), and their pharmaceutically acceptable salts, wherein Y is --CH 2 --, --(CH 2) 2 --, --CH 2 O--, --(CH 2) 2 O-- or --CH 2 S--; R is --CH or --CONH 2 ; and R 1 is a group of formula (a), where R 2 and R 3 are each independently H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --(CH 2) n OH, halo, trifluoromethyl, cyano, --(CH 2) n NR 4 R 5, --CO(C 1 -C 4 alkyl), --OCO(C 1 -C 4 alkyl), --CH(OH)(C 1 -C 4 alkyl), --C(OH)(C 1 -C 4 alkyl 2, --SO 2 NH 2, --(CH 2) n CONR 6 R 7 or --(CH 2) n COO(C 1 -C 4 alkyl); R 4 is H or C 1 -C 4 alkyl; R 5 is H, C 1 -C 4 alkyl or C 1 -C 4 alkysulphonyl; R 6 and R 7 are each independently H or C 1 -C 4 alkyl; and n is 0, 1 or 2. The compounds are particularly useful in treating irritable bowel syndrome.