Water → HCID 86622336, compound

HRID 501703Notes

Reaction equation

HRID 501703 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][C@@H:7]1[OH:17])=[O:4].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24].O>CN(C=O)C>[CH2:24]([O:17][C@H:7]1[CH2:8][C:9]2[C:14](=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C@H:6]1[NH:5][C:3](=[O:4])[C:2]([F:18])([F:19])[F:1])[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86622335HCID 86622335, compound

Product 1

HCID 86622336HCID 86622336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step AE (2): To a solution of 2,2,2-trifluoro-N-((1R,2S)-2-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-yl)acetamide in DMF (4.5 mL) at rt was added sodium hydride (95% purity, 205 mg). The resulting mixture was stirred at rt for 5 min. Allyl bromide (0.26 mL) was added, and the reaction mixture was stirred for 30 min. Water was added, the aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give N-((1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide as a slightly yellowish oil (660 mg). 1H NMR (400 MHz, CDCl3) δ 7.14 (1H, d), 6.85 (1H, d), 6.83 (1H, s), 5.88 (1H, m), 5.44 (1H, d), 5.28 (1H, dt), 5.12 (1H, dt), 4.38 (1H, q), 4.06 (1H, m), 3.76 (3H, s), 3.05 (1H, d).

Workup

  1. stirringthe reaction mixture was stirred for 30 min
  2. extractionthe aqueous layer was extracted with EtOAc (×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4ff3c9d7cd6142b1aba765f428e130b5
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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