Cesium fluoride → HCID 20748290, compound

HRID 1759678Notes

Reaction equation

HRID 1759678 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@H:8]([N:13]1[CH2:18][CH2:17][C:16]3([CH2:23][C@@H:22]([O:24][Si](C(C)(C)C)(C)C)[C:21]4[CH:32]=[C:33]([NH:36]S(C([Si](C)(C)C)C)(=O)=O)[CH:34]=[CH:35][C:20]=4[O:19]3)[CH2:15][CH2:14]1)[CH2:7][CH2:6]2)#[N:2].[F-].[Cs+]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@H:8]([N:13]1[CH2:18][CH2:17][C:16]3([CH2:23][C@@H:22]([OH:24])[C:21]4[CH:32]=[C:33]([NH2:36])[CH:34]=[CH:35][C:20]=4[O:19]3)[CH2:15][CH2:14]1)[CH2:7][CH2:6]2)#[N:2]

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 20748293HCID 20748293, compound

Product 1

HCID 20748290HCID 20748290, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of N-[1′-(6-cyano-1,2,3,4-tetrahydro-2(R)-naphthalenyl)-3,4-dihydro-4(R)-t-butyldimethylsilyloxyspiro[2H-1-benzopyran-2,4′-piperidin]-6-yl]trimethylsilylethanesulfonamide (0.50 gm, 0.75 mmole) in dimethylformamide (5 mL) under argon was added cesium fluoride (0.34 gm, 2.25 mmole)and the mixture heated to 95° C. for 30 hrs. The reaction was cooled diluted with 10% aqueous sodium bicarbonate (50 mL) and extracted with ethyl acetate (2×50 mL). The organic extracts were dried over sodium sulfate concentrated in vacuo to an oil and purified by flash chromatography using 90/10 dichloromethane/methanol to give N-[1′-(6-cyano-1,2,3,4-tetrahydro-2(R)-naphthalenyl)-3,4-dihydro-4(R)-hydroxyspiro-[2H-1-benzopyran-2,4′-piperidin]-6-yl]amine, (0.218 gm, 80%) as a foam. MS m/z 390 (M+), 1H NMR (CDCL3) δ 1.4-2.2 (9 H, m), 2.6-3.2 (9 H, m), 3.4 (2 H, br s), 4.82 (1 H, br t), 6.60 (1 H, dd, J=9.3 and 2.8 Hz), 6.71(1 H, d, J=9.3 Hz), 6.81 (1 H, d, J=2.8 Hz), 7.18 (1 H, d, J=9.3 Hz), 7.37 (2 H, m).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo to an oil
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9a0ffd4a9d1d42068f9a59daae8a18bb
Source dataset
uspto-grants-2005_01
Patent number
US06838291B2

Reaction notes

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