Benzyl Alcohol → [8-(4-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-carbamic acid benzyl ester

HRID 2370295ノート

反応式

HRID 2370295 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(O)=O)[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:45]([O:52][C:26](=[O:35])[NH:23][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:16][CH2:17]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 122302461,4-Dioxaspiro[4.5]decane-8-carboxylic acid, 8-(4-fluorophenyl)-

生成物 1

HCID 59226068[8-(4-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-carbamic acid benzyl ester

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3 g of 8-(4-Fluoro-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid (75) and 3.3 mL of triethyl amine were dissolved in 50 mL of dry toluene. At 0° C. 2.83 mL of diphenyl phosphoryl azide was added dropwise. The mixture was stirred at room temperature until conversion was complete, then the solution was heated to 90° C. until gas evolution stopped. 3.4 mL of benzyl alcohol were added and stirring at 90° C. was continued for another 18 h. The mixture was allowed to cool down to room temperature and 500 mL of ethyl acetate were added. The organic layer was extracted two times with 1N HCl and once with brine, dried over magnesium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography to give 2.85 g of the desired product. Rt=2.52 min (Method E). Detected mass: 386.2 (M+1H+).

後処理

  1. customAt 0° C
  2. temperaturethe solution was heated to 90° C. until gas evolution
  3. stirringstirring at 90° C.
  4. temperatureto cool down to room temperature
  5. extractionThe organic layer was extracted two times with 1N HCl
  6. dry with materialonce with brine, dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe crude product was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-8b7e43a254024eafab7deaeb59782eb3
出典データセット
uspto-grants-2014_04
特許番号
US08710077B2

反応ノート

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