Dimethyl Sulfoxide → 3-Benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde

HRID 2079778ノート

反応式

HRID 2079778 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH:22]2[CH:20]([CH:21]2[CH2:24][OH:25])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([N:18]1[CH2:23][CH:22]2[CH:20]([CH:21]2[CH:24]=[O:25])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20089904(3-Benzyl-3-azabicyclo[3.1.0]hexan-6-yl)methanol

生成物 1

HCID 200899113-Benzyl-3-azabicyclo[3.1.0]hexane-6-carbaldehyde収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-65 °C

実験手順

Oxalyl chloride (0.88 ml, 17.73 mmol) was added to a stirred flask of DCM (100 ml) under N2 and the solution cooled to an internal temperature of −65° C. DMSO (1.26 ml, 17.73 mmol) was then added dropwise, keeping the internal temperature at −65° C. or below at all times. A solution of (3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)methanol (2.00 g, 9.85 mmol) in DCM (50 ml) was then added to the reaction mixture slowly, again making sure the internal temperature did not rise above −65° C. After this addition was complete, triethylamine (5.90 ml, 42.35 mmol) was slowly added to the reaction, again making sure the internal temperature did not rise above −65° C. After addition was complete the reaction was allowed to warm up to r.t. and solvent removed in vacuo. The residue was purified by column chromatography (25% EtOAc in heptane) to give the title compound as a light yellow oil (1.49 g, 76%). LCMS purity 90%, m/z 202 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 2.11 (2H, m), 2.44 (1H, m), 2.50 (2H, d, J=9.3 Hz), 3.07 (2H, d, J=9.3 Hz), 3.64 (2H, s), 7.21-7.35 (5H, m), 9.31 (1H, d, J=4.8 Hz).

後処理

  1. customat −65° C. or below
  2. customdid not rise above −65° C
  3. additionAfter this addition
  4. customdid not rise above −65° C
  5. additionAfter addition
  6. temperatureto warm up to r.t.
  7. customsolvent removed in vacuo
  8. customThe residue was purified by column chromatography (25% EtOAc in heptane)

出典と根拠

ORDレコード
ord-20d65823b8ee44839fa8a5dd73b8f1a9
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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