Formaldehyde → (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Temperature

70 °C

(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 6n (1.21 g, 1.63 mmol) was dissolved in 12 mL 1,4-dioxane, followed by addition of 2.65 mL 37% formaldehyde solution and dropwise addition of 4.89 mL 1 M sodium hydroxide. The reaction mixture was stirred for 16 hours at 70° C. Thereafter, the reaction mixture was concentrated under reduced pressure and was partitioned after 30 mL of saturated sodium chloride solution were added. The aqueous phase was extracted with ethyl acetate (30 mL×3) and the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydro-pyran-2-carbaldehyde 6p (1.27 g, pale yellow grease), which was used directly in the next step without purification.

1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
2. customwas partitioned after 30 mL of saturated sodium chloride solution
3. additionwere added
4. extractionThe aqueous phase was extracted with ethyl acetate (30 mL×3)
5. extractionthe organic extract
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-1616b062f7164aa49d43eafbb0dd5ff5

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2