Formaldehyde → 4-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

HRID 1093972

반응식

HRID 1093972 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7]([Si:10]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)([CH3:9])[CH3:8].[CH2:22]=O.[OH-].[Na+]>C(O)(=O)C.O>[CH:19]([Si:10]([CH:7]([CH3:9])[CH3:8])([CH:16]([CH3:18])[CH3:17])[N:11]1[CH:15]=[CH:14][C:13]([CH2:22][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:12]1)([CH3:21])[CH3:20]

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 145136N-Triisopropylsilylpyrrole

생성물 1

HCID 666367604-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

To a solution of morpholine (98.5 mmoles) in acetic acid (100 ml) at 0° C. there are added 1-triisopropylsilanyl-1H-pyrrole (89.5 mmoles) and formaldehyde (89.5 mmoles) 37% in water. The reaction mixture is stirred overnight at ambient temperature. The solution is brought to alkaline pH (10-12) using 20% aqueous NaOH solution and is then extracted with DCM. The organic phase is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product, which is used directly in the next Step.

후처리

  1. extractionis then extracted with DCM
  2. washThe organic phase is washed with water and with saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue obtained
  7. customis purified by flash chromatography on silica gel (SiO2; gradient DCM/AcOEt)

출처 및 근거

ORD 기록
ord-54b2d334f85d4838b10f400874ce569a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133889B2

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