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

HRID 1618781노트

반응식

HRID 1618781 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff9a0c077d5f43c687d2ca3a96c8ec95
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

반응 노트

불러오는 중…