Triethylamine → HCID 67031170、化合物

HRID 969963ノート

反応式

HRID 969963 の反応式
[CH3:1][O:2][C:3]([C:5]1(C(O)=O)[C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:4].C1C=CC(P([N:28]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[ClH:38].O1CCOCC1>CC(O)(C)C>[ClH:38].[CH3:1][O:2][C:3]([C:5]1([NH2:28])[C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1)=[O:4]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 204431481,4-Dioxane hydrochlorideHCID 20767963445306-40-1

生成物 1

HCID 67031170HCID 67031170、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a mixture of spiro[2,3]hexane-1,1-dicarboxylic acid methyl ester (660 mg, 3.58 mmol) in 3 mL of anhydrous t-BuOH was added 1.08 g (3.92 mmol) of DPPA and 440 mg (4.35 mmol) of Et3N. The mixture was heated at reflux for 21 h and then partitioned between H2O and ether. The ether phase was dried over magnesium sulfate, filtered and concentrated in vacuo to yield an oil. To this oil was added 3 mL of a 4 M HCl/dioxane solution. This acidic solution was stirred at rt for 2 h and then concentrated in vacuo. The residue was triturated with ether to give 400 mg (58%) of desired product as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 8.96 (br s, 3H), 3.71 (s, 3H), 2.41 (m, 1H), 2.12 (m, 4H), 1.93 (m, 1H), 1.56 (q, 2 H, J=8 Hz). LC-MS of free amine: MS m/z 156 (M++1).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 21 h
  3. custompartitioned between H2O and ether
  4. dry with materialThe ether phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield an oil
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-0e38f5973b87407180edee216ec1324e
出典データセット
uspto-grants-2007_12
特許番号
US07309708B2

反応ノート

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