Sodium Carbonate → HCID 68519937, compound

HRID 1931869Notes

Reaction equation

HRID 1931869 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)([F:28])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluoride2×HCID 19935801HCID 19935801, compound

Product 1

HCID 68519937HCID 68519937, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 1-benzyl-3-(3,5-difluorophenyl)pyrrolidin-3-ol (1.9 g, 6.6 mmol) in dichloromethane (20 mL) was added dropwise diethylaminosulphurtrifluoride (1.05 mL, 7.26 mmol) dissolved in dichloromethane (5 mL) and the mixture was stirred at ambient temperature for 1 h. Additional diethylaminosulphurtrifluoride (0.1 mL, 0.69 mmol) was added and stirring was continued 0.5 h. Aqueous sodium carbonate (10%, 50 mL) was added and the phases separated. The aqueous phase was extracted with dichloromethane (50 mL) and the pooled organic phase was dried (MgSO4) and evaporated. Purification by flash column chromatography gave the title compound (0.65 g). MS m/z (rel. intensity, 70 eV) 291 (M+, 44), 200 (17), 133 (51), 132 (45), 91 (bp).

Workup

  1. stirringstirring
  2. waitwas continued 0.5 h
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with dichloromethane (50 mL)
  5. dry with materialthe pooled organic phase was dried (MgSO4)
  6. customevaporated
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-05998c6f2f8c4281b1d3ebc45e4358c9
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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