Formaldehyde → Tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate

HRID 1618781Notes

Reaction equation

HRID 1618781 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:18])[N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].C=O.[C:27]([O-])(O)=[O:28].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][OH:22])([CH2:27][OH:28])[C:7](=[O:18])[N:8]2[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 58154275tert-Butyl 6-bromo-2-oxoindoline-1-carboxylate

Product 1

HCID 58221668Tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (5.20 g, 16.7 mmol) in THF (100 mL) was added potassium carbonate (6.91 g, 50.0 mmol) followed by paraformaldehyde (12.00 g, 400 mmol). The resulting suspension was stirred at rt for 90 min. The suspension was cooled and poured into saturated aqueous NaHCO3 and extracted with DCM. Organic extracts were purified by column chromatography (eluting with a gradient of 0-10% MeOH in DCM) to give tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (1H, s), 7.41 (2H, br. s.), 4.97 (2H, t, J=5.18 Hz), 3.63-3.76 (4H, m), 1.57 (s, 9H).

Workup

  1. temperatureThe suspension was cooled
  2. extractionextracted with DCM
  3. customOrganic extracts were purified by column chromatography (
  4. washeluting with a gradient of 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-ff9a0c077d5f43c687d2ca3a96c8ec95
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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