Water → HCID 58896161, compound

HRID 2422355Notes

Reaction equation

HRID 2422355 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:21]#[N:22])([C:14]2[C:15](Cl)=[N:16][CH:17]=[CH:18][CH:19]=2)[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.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:14]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=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 56651731HCID 56651731, compound

Product 1

HCID 58896161HCID 58896161, compoundYield 101.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-chloro-4′-cyano-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (6 g) and lithium tri-tert-butoxyaluminohydride (72.34 ml), 1M solution in THF) in 1-4-dioxane (90 ml) was refluxed overnight. After cooling, 1 N NaOH (100 ml) and H2O (100 ml) were added slowly at 0° C. Dichloromethane was added to the mixture. The aqueous phase was extracted twice with dichloromethane 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; dichloromethane-methanol (95:5)] to give 5.5 g (46%) of 7-Aza- spiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butylester; MS (ES+) 290 (M+H+).

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter cooling
  3. extractionThe aqueous phase was extracted twice with dichloromethane
  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; dichloromethane-methanol (95:5)]

Sources & evidence

ORD record
ord-217496d4dfda46a9b67c5cd9f8f435d2
Source dataset
uspto-grants-2011_06
Patent number
US07960401B2

Reaction notes

Loading…