tert-Butyldimethylsilyl chloride → HCID 86685131, compound

HRID 1913026Notes

Reaction equation

HRID 1913026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]2[O:29][CH2:28][CH2:27][C:26]=2[CH:30]=1.[C:31]([Si:35]([CH3:38])([CH3:37])Cl)([CH3:34])([CH3:33])[CH3:32]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:35]([O:18][CH2:17][C@H:10]1[O:9][C@:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:29][CH2:28][CH2:27][C:26]=4[CH:30]=3)[CH:4]=2)([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@@H:11]1[OH:16])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:38])[CH3:37]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 68015078HCID 68015078, compound

Product 1

HCID 86685131HCID 86685131, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 5e (6.3 g, 14.44 mmol) was dissolved in 60 mL pyridine, followed by addition of 4-dimethylamino pyridine (353 mg, 2.89 mmol) and tert-butyl-dimethyl-chloro-silane (2.61 g, 17.32 mmol) in turn. The reaction mixture was stirred for 16 hours and concentrated under reduced pressure. The resulting residue was dissolved in 200 mL ethyl acetate and partitioned. The organic extract was washed with water (50 mL) and saturated sodium chloride solution (50 mL), combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 5f (7.96 g, pale yellow solid), which was used directly in the next step without purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 200 mL ethyl acetate
  3. custompartitioned
  4. extractionThe organic extract
  5. washwas washed with water (50 mL) and saturated sodium chloride solution (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a1e65cb967c40c9a1884222b890bcf4
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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