tert-Butanol → [4-(4-Chloro-phenyl)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 510759ノート

反応式

HRID 510759 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11](C(O)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:25]C1C=CC=CC=1.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([NH:19][C:22](=[O:25])[O:47][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 27357924-(4-Chlorophenyl)cyclohexane-1-carboxylic acid

生成物 1

HCID 67080532[4-(4-Chloro-phenyl)-cyclohexyl]-carbamic acid tert-butyl ester収率 57%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-(4-chlorophenyl)cyclohexanecarboxylic acid (1.01 g, 4.231 mmol) and triethylamine (0.5897 ml, 4.231 mmol) in tert-butanol (22 ml) was added diphenyl phosphorazidate (0.9147 ml, 4.231 mmol), and the reaction was heated to reflux for 16 hours. The reaction was diluted with EtOAc and washed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was on a Biotage SP1 system eluting with a linear gradient of 5-50% EtOAc in hexanes to yield 760 mg of the title compound (57% yield).

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 16 hours
  3. washwashed with 1M hydrochloric acid, saturated sodium bicarbonate, and saturated sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluting with a linear gradient of 5-50% EtOAc in hexanes

出典と根拠

ORDレコード
ord-df023823a89443089203c2a05791db88
出典データセット
uspto-grants-2015_08
特許番号
US09096567B2

反応ノート

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