4-pyrrolidin-1-ylbutan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared using the product of step (i) (50 mg), 4-(pyrrolidin-1-yl) butan-1-ol (64.2 mg) and the method of example 74 step (iii) to give a tan solid, 9 mg. the method of example 74 step (iii) to give a tan solid, 9 mg

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

Procedure: The title compound was prepared using the product of step (i) (50 mg), 4-(pyrrolidin-1-yl) butan-1-ol (64.2 mg) and the method of example 74 step (iii) to give a tan solid, 9 mg. the method of example 74 step (iii) to give a tan solid, 9 mg

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

Procedure: 4-Oxo-4-(1-pyrrolidinyl)butyric acid (0.30 g; 1.75 mmol) in 10 mL of THF in an argon-filled flask was treated with lithium aluminum hydride (0.17 g; 4.38 mmol) at 70° C. for 4 h. After cooling the mixture to room temperature, hydrolysis was effected by addition of 0.17 mL each of water and 5 N NaOH, followed by 0.51 mL of water. Stirring was continued for 0.5 h. The mixture was filtered and concentrated under reduced pressure to give the title compound as a colorless oil (0.21 g; 84% yield). hydrolysis The mixture was filtered concentrated under reduced pressure

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

Procedure: Sodium hydride (49 mg of 60% NaH in mineral oil; 1.23 mmol) was suspended in 3 mL of dry DMF in a flame-dried, argon-filled flask. After stirring for 15 min, a solution of 4-(1-pyrrolidinyl)butanol (Part B) in 1 mL of dry DMF was added. After stirring for 15 min and gas evolution had ceased, 4-fluorophenyl 2-[4-[2-(1-pyrrolidinyl)ethoxyl]phenyl]benzo[b]thiophen-3-yl ketone (Part A) (0.2 g; 0.49 mmol) in 1 mL of dry DMF was added. The mixture was stirred at room temperature for 5 h, then poured into 25 mL of water. Extraction was carried out with Etoac (4×25 mL). The combined organics were washed with brine and dried by passage through sodium sulfate. The title compound (0.18 g; 66% yield) was isolated as a colorless oil by flash chromatography on silica gel, eluting with a gradient of EtOAc(100-85%)/Et3N(0-5%)/MeOH(0-10%). Conversion to the dioxalate was effected as in Example 137, Part E. filled flask After stirring for 15 min The mixture was stirred at room temperature for 5 h Extraction The combined organics were washed with brine dried by passage through sodium sulfate