(2-methyloxolan-2-yl)methanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (+)-enantiomer was processed to Isomer II; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (−)-enantiomer was processed to Isomer I; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (+)-enantiomer was processed to Isomer II; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (−)-enantiomer was processed to Isomer I; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (+)-enantiomer was processed to Isomer II; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in analogy to example 7, using 3-oxo-butyric acid methyl ester as compound of formula R, 2-bromo-1-[2-chloro-5-(trifluoromethyl)-phenyl]-ethanone as compound of formula S, tetrahydro-2-methyl-2-furanmethanamine as R3—(CH2)m—NH2 and (1R,2R)-2-aminocyclohexanol as R1R2NH. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane) and the (−)-enantiomer was processed to Isomer I; MS (ISP) 499.4 (M+H)+. Enantiomers of the 5-(2-chloro-5-trifluoromethyl-phenyl)-2-methyl-1-(−2-methyl-tetrahydro-furan-2-ylmethyl)-1H-pyrrole-3-carboxylic acid methyl ester were separated on ChiralPak AD (2% isopropanol/heptane)