Sodium Carbonate → HCID 86643426, compound

HRID 1931870Notes

Reaction equation

HRID 1931870 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2(O)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(S(F)(F)[F:28])CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([F:28])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 68518913HCID 68518913, compound

Product 1

HCID 86643426HCID 86643426, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of tert-butyl 3-(3,5-dichlorophenyl)-3-hydroxypyrrolidin-1-carboxylate (0.88 g, 2.65 mmol) in dichloromethane (50 mL) was added dropwise diethylaminosulphurtrifluoride (0.35 mL, 2.65 mmol) dissolved in dichloromethane (20 mL) and the mixture was stirred at 0° C. for 20 minutes and at ambient temperature for 10 minutes. Aqueous sodium carbonate (10%, 50 mL) was added and the phases separated. The aqueous phase was extracted with dichloromethane (2×50 mL) and the pooled organic phase was dried (Na2SO4) and evaporated. Purification by flash column chromatography gave the title compound (0.45 g). MS m/z (rel. intensity, 70 eV) 334 (M+, 1), 278 (8), 277 (6), 260 (8), 57 (bp).

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×50 mL)
  3. dry with materialthe pooled organic phase was dried (Na2SO4)
  4. customevaporated
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-60b9527d5fa7474890a521e55b7cc50f
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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