118535-72-1

Basic information

• Product Name: 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine
• Synonyms: 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine
• CAS NO: 118535-72-1
• Molecular Weight: 296.369
• Mol File: 118535-72-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine(118535-72-1)
• EPA Substance Registry System: 1-nitroso-2-(1'-methoxy-1',1'-diphenyl)pyrrolidine(118535-72-1)

Safety Data

• Hazardous Substances Data: 118535-72-1(Hazardous Substances Data)

Upstream product

• 118535-80-1 (R)-2-[(E)-(S)-2-(Methoxy-diphenyl-methyl)-pyrrolidin-1-ylimino]-1,3-diphenyl-propan-1-ol 
• 220956-07-0 [(S)-2-Benzyl-2-benzyloxy-3,3,3-trifluoro-prop-(E)-ylidene]-[(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-yl]-amine 
• 220956-08-1 (2S,2'S)-1-[2'-benzyloxy-2'-phenyl-3',3',3'-(trifluoro)propyleneamino]-2-(1''-methoxy-1'',1''-diphenyl)pyrrolidine 
• 220956-09-2 [(S)-2-Benzyloxy-2-trifluoromethyl-non-(E)-ylidene]-[(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-yl]-amine 
• 118535-65-2 (1-Benzyl-2-phenyl-ethylidene)-[(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-yl]-amine 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 
• 147-85-3 L-proline 
• 118970-99-3 (S)-(-)-1-benzyl-2-(1-methoxy-1,1-diphenylmethyl)-pyrrolidine 
• 118970-95-9 (S)-1-benzyl-2-(hydroxydiphenylmethyl)pyrrolidine 
• 955-40-8 N-benzyl-L-proline ethyl ester 
• 220956-02-5 (S)-1,1,1-Trifluoro-2-{[(E)-(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-ylimino]-methyl}-nonan-2-ol 
• 220955-98-6 (S)-2-Benzyl-1,1,1-trifluoro-3-[(E)-(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-ylimino]-propan-2-ol 
• 220956-00-3 (S)-1,1,1-Trifluoro-3-[(E)-(S)-2-(methoxy-diphenyl-methyl)-pyrrolidin-1-ylimino]-2-phenyl-propan-2-ol 
• 220955-83-9 (S)-1-methylenamino-2-(1,1-diphenyl-1-methoxymethyl)pyrrolidine 

Downstream Products

• 118535-63-0 (S)-(-)-1-amino-2-(1'-methoxy-1',1'-diphenylmethyl)pyrrolidine 

Relevant articles and documents

Stereoselective Synthesis of Trifluoromethylated Compounds: Nucleophilic Addition of Formaldehyde N,N-Dialkylhydrazones to Trifluoromethyl Ketones

The nucleophilic 1,2-addition of formaldehyde N,N-dialkylhydrazones 1, 2, and 7-10 to trifluoromethyl ketones 3a-e takes place in the absence of any catalyst or promoter to afford a series of α-hydroxy-α-trifluoromethylhydrazones (4, 5, and 11-14) in good-to-excellent yields. From the several reagents studied, optimal results were achieved using 1-(methyleneamino)pyrrolidine (2) for the synthesis of racemic adducts and (S)-l-(methyleneamino)-2-[1-(methoxy)diphenyl-methyl]-pyrrolidine (10) for the asymmetric version of the reaction. The resolving properties of the chiral auxiliary carried by 10 allowed an easy Chromatographic (flash) separation of any obtained diastereomeric mixture. Thus, a single operation rendered moderate-to-good amounts (42-75%) of optically pure adducts (S,S)-14 (de > 98%) by combining excellent chemical (82-92%) and moderate optical (51-81%) yields. Hydrazones 5 and (S,S)-14 were protected by benzylation [→ 16 and (SJS)-18] and then transformed into benzyl-protected α-trifluoromethyl cyanohydrins 21 by MMPP oxidative cleavage and into α-benzyloxy-a-trifluoromethyl aldehydes 22 by ozonolysis. Alternatively, adducts 5 and (S,S)-14 were methylated [→ 19 and (S,S)-20] and transformed into the corresponding α-methoxy-α-trifluoromethyl carboxylic acids 24 by successive ozonolysis and in situ oxidation (NaClO2, tBuOH, isobutene) of the crude a-methoxyaldehydes.

LARGE SCALE PREPARATION OF VERSATILE CHIRAL AUXILIARIES DERIVED FROM (S)-PROLINE

The synthesis of a variety of enantiomerically pure chiral auxiliaries based on (S)-proline and bearing sterically demanding side chains at the pyrrolidine moiety, such as the secondary amines (S)-3,5 and 7 and the hydrazines (S)-6, is described on a molar scale.As key step, the Grignard or RLi addition to the N-benzylated proline ester (S)-1 is used.