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

HRID 2079777ノート

反応式

HRID 2079777 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d8ec6f293cd34bc59d8277ace0083a8d
出典データセット
uspto-grants-2011_04
特許番号
US07932246B2

反応ノート

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