Ethyl 8-(cyanomethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

HRID 1023642

反応式

HRID 1023642 の反応式
C([O:3][C:4]([C:6]1([CH2:16][C:17]#[N:18])[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)=O)C.[H][H]>CO.C(O)(=O)C>[O:13]1[C:9]2([CH2:14][CH2:15][C:6]3([CH2:16][CH2:17][NH:18][C:4]3=[O:3])[CH2:7][CH2:8]2)[O:10][CH2:11][CH2:12]1

参加物

5

反応物 2

HCID 58230182Ethyl 8-(cyanomethyl)-1,4-dioxaspiro[4.5]decane-8-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 582301081,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one収率 38.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

8-Cyanomethyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (525 mg) was dissolved in methanol (10 mL) and acetic acid (5 mL). Platinium(IV) oxide (235 mg) was added and an atmosphere of hydrogen was introduced. The mixture was then stirred at RT for 18 hours. The reaction was filtered over dicalite speed plus (Acros Organics) and the filtrate was concentrated in vacuo. The residue was poured into ice/water and was basified with 2M aqueous NaOH solution. The aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the title compound as a colorless solid (169 mg). MS (ESI): 212.2 (MH+.

後処理

  1. filtrationThe reaction was filtered over dicalite speed plus (Acros Organics)
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was poured into ice/water
  4. extractionThe aqueous layer was extracted two times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-e595911dc2a94d4495243478b4ca0e86
出典データセット
uspto-grants-2014_05
特許番号
US08722721B2

関連ノート

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