(1R,2R,3S,5S)-2-Hydroxy-6-oxabicyclo[3.1.0]hexane-3-Methanol synthesis

Yield:905580-84-9 76%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 20; for 4 h;

Steps:

76.a

Example 76: ((lS,2S,4R)-4-{4-[(lS)-2,3-Dihydro-lH-inden-l-ylamino]-7H-pyrrolo[2,3-d]- pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl sulfamateStep a: (lii2R,35,55)-3-(Hydroxymethyl)-6-oxabicyclor3.1.0]hexan-2-ol; [0575] To a solution of (lS,5S)-5-(hydroxymethyl)cyclopent-2-en-l-ol (3.19 g, 27.9 mmol) (An, G.-L; Rhee, H. Nucleosides Nucleotides 2002, 21, 65-72) in DCM (143 mL) at 0 ⁰C was added 3-chloroperbenzoic acid (7.52 g, 33.5 mmol) and the mixture was stirred at room temperature for 4 hours. Silica gel (20 g) was added, the mixture was concentrated to dryness and was purified via flash chromatography (0 to 100% EtOAc/DCM) to afford the title compound (2.75g, 76%).[0576] LCMS: R.t. 0.37 min ES+ 131 (ammonium acetate) .

References:

WO2006/84281,2006,A1 Location in patent:Page/Page column 136