Sodium Hydroxide → HCID 67284959, compound

HRID 1618792Notes

Reaction equation

HRID 1618792 reaction equation
[CH3:1][C:2]1([CH3:23])[O:22][CH2:21][C:5]2([C:13]3[C:8](=[CH:9][C:10]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)=[CH:11][CH:12]=3)[NH:7][C:6]2=O)[CH2:4][O:3]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:23])[O:3][CH2:4][C:5]2([C:13]3[C:8](=[CH:9][C:10]([N:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)=[CH:11][CH:12]=3)[NH:7][CH2:6]2)[CH2:21][O:22]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 67284582HCID 67284582, compound

Product 1

HCID 67284959HCID 67284959, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indolin]-2′-one (0.11 g, 0.35 mmol) in toluene (14 mL) was added sodium bis(2-methoxyethoxy)aluminium hydride (60% in toluene, 0.53 mL, 1.74 mmol). After stirring at 80° C. for 40 min, the solution was poured into a mixture of ice and 2N NaOH. The product was extracted with DCM and the combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (eluting with a gradient of 5-60% EtOAc in hexanes) gave 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indoline] as a white solid. Mass Spectrum (ESI) m/e=305.2 (M+1).

Workup

  1. extractionThe product was extracted with DCM
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by column chromatography (
  6. washeluting with a gradient of 5-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d26d51b5318647488b097138cc43d970
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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