(3R,4R)-(-)-1-BENZYL-3,4-PYRROLIDINDIOL

off-white to light brown powder

Borane in THF (1.0 M) (17.19 mL, 180.99 mmol) was added drop-wise to a solution of 2a (10.0 g, 45.24 mmol) in THF (200 mL) at RT, after completion of addition, reaction mixture was slowly heated to 70 °C for 3 h. The reaction mixture was cooled to 0 °C, quenched with methanol (50 mL) by the drop-wise addition, slowly warmed to RT, stirred for 1 h. (Note: intensive gas evolution is occurred). The reaction mixture was concentrated in vacuo, crude was purified on a silica gel column using a linear gradient of ethyl acetate in Pet-ether yielding 7.73 g (88.5percent) of yellowish crystals of compound 3a. SOR (MeOH, 0.5percent): +22.800°; Step 2: To a 1, 4-dioxane (20 mL) solution of 1, 4-di-O-tosyl-D-threitol (9.15 g, 21.25 mmol), benzylamine (9.29 mL, 85.0 mmol) was added, and the mixture was heated to reflux under a nitrogen stream for 4 days while stirring. The reaction liquor was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography using silica gel [NH(basic)-silica gel 100 g, ethyl acetate to chloroform/methanol (10/1)], to obtain the title compound (1.88 g, 46percent) as an oily matter. NMR(CDCl

Molecular Weight:193.24
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:193.110278721
Monoisotopic Mass:193.110278721
Topological Polar Surface Area:43.7
Heavy Atom Count:14
Complexity:170
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes