Methanol → HCID 68556192, compound

A solution of tert-butyl 4-(2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidine-1-carboxylate (1.0 g, 2.440 mmol) in anhydrous CH2Cl2 (20 mL) was treated with sodium borohydride (0.055 g, 1.464 mmol), followed by anhydrous MeOH (4 mL). The mixture was stirred at RT for 1.5 h and then concentrated on a rotary evaporator. The resultant residue was treated with 4 M HCl in dioxane (10 mL). After stirring for 2 h, the mixture was concentrated and this residue was made basic with a minimum amount of saturated NaHCO3. The mixture was lyophilized. The resultant lyopholate was treated with CH2Cl2 (50 mL), stirred vigorously for 5 minutes, and then filtered (CH2Cl2 washes). The combined CH2Cl2 filtrates were concentrated to give 2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(piperidin-4-yl)ethanol (0.79 g, 2.53 mmol, 104% yield) as an off-white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 4.09-4.17 (1 H, m), 3.95-4.02 (1 H, m), 3.86 (1 H, ddd, J=8.84, 6.21, 2.31 Hz), 3.11-3.19 (2 H, m), 2.62 (2 H, tt, J=12.28, 3.10 Hz), 2.29 (3 H, s), 1.84 (1 H, d, J=12.96 Hz), 1.64-1.71 (1 H, m), 1.55-1.64 (1 H, m), 1.34-1.44 (2 H, m).

1. concentrationconcentrated on a rotary evaporator
2. additionThe resultant residue was treated with 4 M HCl in dioxane (10 mL)
3. stirringAfter stirring for 2 h
4. concentrationthe mixture was concentrated
5. additionThe resultant lyopholate was treated with CH2Cl2 (50 mL)
6. stirringstirred vigorously for 5 minutes
7. filtrationfiltered (CH2Cl2 washes)
8. concentrationThe combined CH2Cl2 filtrates were concentrated

ORD record

ord-aceec51661e24bfda50a248384f4e59c

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354432B2