Water → HCID 58557434, compound

Temperature

-20 °C

To a solution of 2-ethyl-4-(methoxycarbonyl)cyclopentanecarboxylic acid (8.34 g, 41.7 mmol, Preparation #11, Step A) in THF (208 mL) was added LiBH4 (0.907 g, 41.7 mmol) at about −20° C. The reaction mixture was stirred at about −20° C. for about 1 h. The reaction mixture was allowed to warm to about 25° C. then was stirred at about 25° C. for about 16 h. Additional LiBH4 (0.907 g, 41.7 mmol) was added. The reaction mixture was stirred at about 25° C. for about 4 h. Water (10 mL) was added slowly to quench the reaction. The solid was removed by vacuum filtration. The filtrate was concd under reduced pressure. The resulting residue was partitioned between water (50 mL) and DCM (3×50 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylic acid (7.29 g, 100%): LC/MS (Table 1, Method n) Rt=0.44 min; MS m/z: 173 (M−H)+.

1. temperatureto warm to about 25° C.
2. stirringthen was stirred at about 25° C. for about 16 h
3. stirringThe reaction mixture was stirred at about 25° C. for about 4 h
4. customto quench
5. customthe reaction
6. customThe solid was removed by vacuum filtration
7. customThe resulting residue was partitioned between water (50 mL) and DCM (3×50 mL)
8. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
9. filtrationfiltered

ORD record

ord-0ba80d2f0cb54f6d9b39103f20b5ab41

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2