Benzyl Alcohol → (1-Phenyl-cyclohexyl)-carbamic acid benzyl ester

HRID 2235198ノート

反応式

HRID 2235198 の反応式
[C:1]1([C:7]2(C(O)=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1C=CC=CC=1>[CH2:40]([O:47][C:21](=[O:30])[NH:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 708171-Phenylcyclohexane-1-carboxylic acidHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 59299316(1-Phenyl-cyclohexyl)-carbamic acid benzyl ester収率 38%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
80 °C

実験手順

Dissolve 1-phenyl-cyclohexanecarboxylic acid (5.0 g, 24.48 mmol) in benzene (200 mL). Add triethylamine (2.45 g, 24.48 mmol), diphenylphosphoryl azide (6.74 g, 24.48 mmol), and benzyl alcohol (3.97 g, 36.72 mmol) under nitrogen. Stir and heat the reaction mixture to 80° C. Continue to heat the reaction at 80° C. for 8 hours, then cool to room temperature. Add water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane) to give 2.87 g (38%) of the title compound as a colorless oil.

後処理

  1. temperatureto heat
  2. customthe reaction at 80° C. for 8 hours
  3. temperaturecool to room temperature
  4. extractionAdd water (250 mL), and extract the aqueous layer with ethyl acetate (3×300 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify by flash column chromatography (silica gel, 5-25% of EtOAc/Hexane)

出典と根拠

ORDレコード
ord-2fbe188cdd314f84b899a53aec685cf6
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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