Methanesulfonyl chloride → (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl methanesulfonate

HRID 1050249Notes

Reaction equation

[C:1]1([CH:7]2[O:12][C@H:11]3[CH2:13][C@H:14]([OH:17])[CH2:15][O:16][C@@H:10]3[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:18][S:19]([O:17][C@@H:14]1[CH2:15][O:16][C@H:10]2[C@@H:11]([O:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH2:9]2)[CH2:13]1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol (850 mg, 3.60 mmol) and DMAP (22 mg, 0.180 mmol) under nitrogen in anhydrous pyridine (10.0 mL) at 0° C. was added methanesulfonyl chloride (0.51 mL, 742 mg, 6.48 mmol) dropwise over 2 minutes. After stirring at 0° C. for 1.5 hours, the mixture was diluted with toluene (10 mL) and concentrated under reduced pressure. The resultant white solid was dissolved in DCM and filtered to remove solids. The filtrate was then chromatographed using a Biotage™ 50 g silica gel cartridge eluted with 0-50% EtOAc in 1:1 Hexane/DCM over 20 column volumes. The product fractions were combined and concentrated under reduced pressure to provide the title compound as a white solid. LC-MS: calculated for C14H18O6S 314.08, observed m/e: 315.06 (M+H)+ (Rt 1.56/4 min).

Workup

concentrationconcentrated under reduced pressure
dissolutionThe resultant white solid was dissolved in DCM
filtrationfiltered
customto remove solids
customThe filtrate was then chromatographed
washeluted with 0-50% EtOAc in 1:1 Hexane/DCM over 20 column volumes
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-88c28fe1343d4c299e0893e297e4165e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382243B2

Reaction notes

Loading…