Acetaldehyde → HCID 69812790, compound

HRID 2190099Notes

Reaction equation

HRID 2190099 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3Br)[N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30](=[O:32])[CH3:31]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH:30]([OH:32])[CH3:31])[N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 68759234HCID 68759234, compound

Product 1

HCID 69812790HCID 69812790, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl 1′-benzyl-4-bromospiro[indoline-3,4′-piperidine]-1-carboxylate (0.700 g, 1.53 mmol) in THF (10 mL) at −78° C. was treated by the dropwise addition of 1.6M in hexanes n-BuLi (0.673 ml, 1.68 mmol). The mixture was stirred at −78° C. for 30 minutes, and acetaldehyde (0.129 mL, 2.30 mmol) was added neat and stirring was continued an additional 30 minutes at −78° C. The reaction was then stirred at room temperature for 1.5 hours. The reaction was quenched by the addition of saturated NH4Cl, and the reaction was extracted with EtOAc. The combined organics were washed with brine, dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (20 then 50-70% EtOAc/Hexane) to yield pure tert-butyl 1′-benzyl-4-(1-hydroxyethyl)spiro[indoline-3,4′-piperidine]-1-carboxylate (0.491 g, 76%). LCMS (APCI+) m/z 423.2 [M+H]+; Rt=3.66 min

Workup

  1. stirringstirring
  2. waitwas continued an additional 30 minutes at −78° C
  3. stirringThe reaction was then stirred at room temperature for 1.5 hours
  4. customThe reaction was quenched by the addition of saturated NH4Cl
  5. extractionthe reaction was extracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (20

Sources & evidence

ORD record
ord-8bd1e710ea5e4c488ec8d93bd258ecf4
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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