Methanol → HCID 118045109, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-benzyloxyphenyl)methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (1.00 equiv; 1.05 moles; 692.80 g), methanol (85.59 moles; 3.46 L; 2.74 kg), and tetrahydrofuran (42.57 moles; 3.46 L; 3.07 kg) add ammonium formate (5.27 moles; 332.10 g). Purge the reaction vessel with nitrigen and add 5% palladium on charcoal (69.30 g; Johnson Matthey type 87 L, 57.8% moisture content) as a slurry in isopropyl alcohol. Heat the mixture at 38-42° C. for 15 mins (moderate bubbling observed). Remove the heating bath and stir the reaction mixture for 15 minutes whilst cooling. Filter the mixture through diatomaceous earth and concentrate the filtrate under reduced pressure. Partition the residue between ethyl acetate (7.5 L) and water (1 L). Separate the organic layer and wash with brine then dry over MgSO4. Filter, and concentrate under reduced pressure to give the title compound (594 g; 99% yield) mass spectrum (m/z): 568.2 (M+1) and 590.2 (M+23).

Provenance & Evidence