Hydrochloric Acid → HCID 178520920, compound

Temperature

-10 °C

To a stirred solution of methyl trans-4-(4-chlorophenyl)cyclohexanecarboxylate (compound of formula (VIIa)) (25.3 g, 100 mmol) in dichloromethane (250 mL) at −78° C. under argon was added a 1M solution of diisobutylaluminium hydride (DIBAL) in dichloromethane (110 mL, 110 mmol) and the mixture was stirred for 90 minutes. A further 5 mLs of DIBAL was then added. Methanol (125 mL) was added with stirring and the mixture allowed to warm to −10° C. 1M aqueous hydrochloric acid (250 mL, 250 mmol) was then added with stirring. The aqueous layer was extracted with dichloromethane (250 mL) and the combined organics washed twice with water (2×125 mL). The organics were concentrated under vacuum to a volume of 75 mL, the residue was diluted by the addition ethyl acetate (125 mL) and the mixture was then concentrated under vacuum to a volume of 75 mL. The resulting mixture containing the title compound was used in the next step without analysis or purification.

1. stirringwith stirring
2. stirringwith stirring
3. extractionThe aqueous layer was extracted with dichloromethane (250 mL)
4. washthe combined organics washed twice with water (2×125 mL)
5. concentrationThe organics were concentrated under vacuum to a volume of 75 mL
6. additionthe residue was diluted by the addition ethyl acetate (125 mL)
7. concentrationthe mixture was then concentrated under vacuum to a volume of 75 mL
8. additionThe resulting mixture containing the title compound
9. customwas used in the next step without analysis or purification

ORD record

ord-5ea94857666f4b24b501ba58056df58f

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598387B2