Acetone → (1R,2R)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1-oxide

A stirred suspension of sodium borohydride (11.44 g) in ethanol (935 ml) is treated with a solution of crude (R)-6-(3-pyridyl)-3,4-dihydro-2H-thiopyran 1-oxide (116.9 g; prepared as described in Example 10) in ethanol (117 ml) at room temperature under nitrogen. The mixture is stirred for 3 hours and is then treated with water (935 ml) and acetone (93 ml), with cooling. The solution is extracted with dichloromethane (3×800 ml), the combined extracts are washed with aqueous sodium chloride solution (2×800 ml;25% w/v), dried over magnesium sulphate, and evaporated under reduced pressure to give a paste (96.2 g). This paste is recrystallised from a mixture of tert-butyl methyl ether and methyl ethyl ketone, to give (1R,2R)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1 -oxide (36.16 g), in the form of a pale yellow powder, m.p. 121°-126° C., enantiomeric excess 99.6%. [NMR (CDCl3):- 1.6(m, 1H), 1.8(m,2H),2.0(m,1H),2.4(m,1H),2.7(m,2H), 3.2(m,1H),3.5(dd,1H),7.3(m,1H),7.7(dt, 1H), 8.6(m,2H)].

1. temperaturewith cooling
2. extractionThe solution is extracted with dichloromethane (3×800 ml)
3. washthe combined extracts are washed with aqueous sodium chloride solution (2×800 ml;25% w/v)
4. dry with materialdried over magnesium sulphate
5. customevaporated under reduced pressure
6. customto give a paste (96.2 g)
7. customThis paste is recrystallised from a mixture of tert-butyl methyl ether and methyl ethyl ketone

ORD record

ord-9e6a4be1268646989fb9cb31197ed14b

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05780636