Cesium carbonate → HCID 86698695, compound

HRID 338355

Reaction equation

HRID 338355 reaction equation
CS([O:5][CH2:6][C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[Br:19][C:20]1[CH:25]=[CH:24][C:23](O)=[C:22]([O:27][CH3:28])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([O:5][CH2:6][C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:22]([O:27][CH3:28])[CH:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2622344-Bromo-2-methoxyphenolHCID 10039261tert-butyl (2S)-2-[(methanesulfonyloxy)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 86698695HCID 86698695, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-tert-butyl 2-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate (279 mg, 1.00 mmol) and 4-bromo-2-methoxyphenol (325 mg, 1.57 mmol) in N,N-dimethylformamide (5.55 mL) was added cesium carbonate (651 mg, 2.00 mmol). The mixture was heated to 100° C. After 22 h, the mixture was allowed to cool to 23° C. and diluted with water (30 mL). The mixture was extracted with ethyl acetate (3×30 mL). The combined organics were dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo. Purification by column chromatography (silica gel, 0-50% ethyl acetate in dichloromethane) afforded the title compound as an amber oil. MS (ES+) 408.2 (M+Na)+. 1H NMR (400 MHz, CDCl3): δ 7.07-6.79 (m, 3H), 4.25-4.10 (m, 2H), 4.01-3.73 (m, 1H), 3.84 (s, 3H), 3.48-3.26 (m, 2H), 2.16-1.80 (m, 4H), 1.48 (s, 9H).

Workup

  1. temperatureto cool to 23° C.
  2. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customPurification by column chromatography (silica gel, 0-50% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-72787639a3644b2c96e8408ee14b1b16
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Linked notes

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