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

HRID 1050249
Notes
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Reaction equation

HRID 1050249 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58194975(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol

Product 1

HCID 89051399(4aR,7S,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl methanesulfonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent
HCID 1140
Toluene
Solvent

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

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resultant white solid was dissolved in DCM
  3. filtrationfiltered
  4. customto remove solids
  5. customThe filtrate was then chromatographed
  6. washeluted with 0-50% EtOAc in 1:1 Hexane/DCM over 20 column volumes
  7. 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

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