Acetic Acid → 4-Acetyl-1-azabicyclo[2.2.1]heptane

HRID 1587372노트

반응식

HRID 1587372 반응식
[N:1]12[CH2:7][C:4]([C:8](N(OC)C)=[O:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C[Li].[CH3:16]COCC.C(O)(=O)C>C1COCC1>[C:8]([C:4]12[CH2:7][N:1]([CH2:6][CH2:5]1)[CH2:2][CH2:3]2)(=[O:9])[CH3:16]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 156636181-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamideHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 106783104-Acetyl-1-azabicyclo[2.2.1]heptane수율 68.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-40 °C

실험 절차

1-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamide (D21) (10 g, 0.054 mole) was dissolved in dry THF (250 ml) under nitrogen cooled to -40° C. and treated with methyl lithium in ether (55 ml, 1 molar, 0.055 moles). The solution was allowed to warm to room temperature over a period of 1 h. Acetic acid (3.3 ml, leq) was added and the solution concentrated in vacuo to a gum. The residue was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum which was distilled in vacuo to afford 4-acetyl-1-azabicyclo[2.2.1]heptane (D22) (5.15 g, 0.037 mole, 68%).

후처리

  1. temperatureto warm to room temperature over a period of 1 h
  2. concentrationthe solution concentrated in vacuo to a gum
  3. customThe residue was partitioned between chloroform and saturated aqueous potassium carbonate solution
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo to a gum which
  7. distillationwas distilled in vacuo

출처 및 근거

ORD 기록
ord-a83bedb2d94b42de9867b49d3e5739af
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05217975

반응 노트

불러오는 중…