Water → HCID 58896163, compound

HRID 2422357Notes

Reaction equation

HRID 2422357 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:21]#[N:22])([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2F)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[OH-].[Na+].O>C1COCC1.O1CCOCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:14]3[C:19](=[CH:18][N:17]=[CH:16][CH:15]=3)[NH:22][CH2:21]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 16684435Lithium tritertbutoxyaluminohydrideHCID 58896168HCID 58896168, compound

Product 1

HCID 58896163HCID 58896163, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-cyano-3′-fluoro-3,4,5,6-tetrahydro-2H-[4,4′]bipyridinyl-1-carboxylic acid tert-butyl ester (1 g) and lithium tri-tert-butoxyaluminohydride (12.7 ml), 1M solution in THF) in 1-4-dioxane (15 ml) was stirred at 130° C. (sealed tube) for 1 hr. After cooling, 1 N NaOH (100 ml) and H2O (100 ml) were added slowly at 0° C. Ethyl acetate was added to the mixture. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with saturated sodium bicarbonate, dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was purified by chromatography [SiO2; hexane-ethyl acetate (7:3)] to give 230 mg g (24%) of 6-aza-spiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butylester; MS (ES+) 290 (M+H+).

Workup

  1. custom(sealed tube) for 1 hr
  2. temperatureAfter cooling
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washthe combined organic layers were washed with saturated sodium bicarbonate
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography [SiO2; hexane-ethyl acetate (7:3)]

Sources & evidence

ORD record
ord-2be41f8d13564084926268f1e7b01356
Source dataset
uspto-grants-2011_06
Patent number
US07960401B2

Reaction notes

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