Sodium Bicarbonate → HCID 89962321, compound

HRID 337895Notes

Reaction equation

HRID 337895 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[C@H:9]([C:10]2[N:14]([CH3:15])[N:13]=[CH:12][CH:11]=2)[CH2:8][C@H:7](O)[CH2:6]1.COCCN(S(F)(F)[F:27])CCOC.C(=O)([O-])O.[Na+]>ClCCl>[F:27][C@H:7]1[CH2:8][C@H:9]([C:10]2[N:14]([CH3:15])[N:13]=[CH:12][CH:11]=2)[C@@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 89962512HCID 89962512, compound

Product 1

HCID 89962321HCID 89962321, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (1S*,3R*,4S*)-3-(methoxymethoxy)-4-(1-methyl-1H-pyrazol-5-yl)cyclopentanol (150 mg, 0.663 mmol) prepared in Example 106b in dichloromethane (2.0 mL), bis(2-methoxyethyl)amino sulfur trifluoride (0.26 mL, 1.33 mmol) was added with cooling on ice, and the reaction solution was stirred at room temperature for 2 hours. To the reaction solution, an aqueous sodium hydrogencarbonate solution (10 mL) was added, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=2:3) to yield the title compound (132 mg, 87%) as a colorless oil.

Workup

  1. temperaturewith cooling on ice
  2. extractionan organic layer was extracted
  3. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  4. concentrationAfter vacuum concentration
  5. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=2:3)

Sources & evidence

ORD record
ord-080cf6941ea346bcb51a936b174c18e9
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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