Sodium Sulfate → (3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanol

HRID 2079777노트

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HRID 2079777 반응식
[CH2:1]([N:8]1[C:13](=O)[CH:12]2[CH:10]([CH:11]2[C:15](OCC)=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 24436Sodium SulfateHCID 15713436Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 20089904(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanol수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
60 °C

실험 절차

Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate (37.2 g, 136.3 mmol) was dissolved in dry THF (400 ml). This solution was added dropwise at 0° C. to a suspension of LiAlH4 (20.7 g, 545.3 mmol) in dry THF (200 ml). The resulting brown suspension was heated to 60° C. under nitrogen atmosphere for 36 h. The mixture was then cooled to 0° C. and quenched carefully with sat. NH4Cl. A grey solid formed and more THF was added to allow adequate stirring. Solid Na2SO4 was added to the mixture which was stirred at r.t. for 30 min. The mixture was then filtered through celite to give a pale yellow solution. This was concentrated in vacuo to give the title compound as an orange oil (14.1 g, 51%). m/z 204 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 2.25 (2H, d), 2.85 (2H, d), 3.20 (2H, t), 3.55 (2H, s), 4.35 (1H, t), 7.20-7.40 (5H, m).

후처리

  1. temperatureThe mixture was then cooled to 0° C.
  2. customquenched carefully with sat. NH4Cl
  3. customA grey solid formed
  4. filtrationThe mixture was then filtered through celite
  5. customto give a pale yellow solution
  6. concentrationThis was concentrated in vacuo

출처 및 근거

ORD 기록
ord-d8ec6f293cd34bc59d8277ace0083a8d
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932246B2

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