Ammonium Chloride → HCID 178477574、化合物

HRID 853133ノート

反応式

HRID 853133 の反応式
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:41]1([C:44](Cl)=O)[CH2:43][CH2:42]1.[NH4+].[Cl-]>C(Cl)Cl.C1COCC1.CCOCC>[CH2:1]([N:8]([CH2:44][CH:41]1[CH2:43][CH2:42]1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si:25]([CH2:28][CH3:29])([CH2:30][CH3:31])[CH2:26][CH3:27])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178477573HCID 178477573、化合物

生成物 1

HCID 178477574HCID 178477574、化合物収率 110.4%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 930 mg (1.73 mmol) of trans benzyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 3.1) in 2 mL of CH2Cl2 was treated with 0.6 mL (3.5 mmol) of DIPEA and 0.23 mL (2.56 mmol) of cyclopropylcarbonylchloride. The mixture was stirred at RT overnight and distributed between a saturated aqueous solution of NH4Cl and Et2O. The combined organic phases were dried over Na2SO4, and the solvent was evaporated. The crude material obtained was dissolved in 10 mL of THF, treated with 3.46 mL of a 1M BH3-solution in THF and refluxed for 6 hrs. Distribution between a diluted aqueous solution of NaOH and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave 1 g of crude trans benzyl-cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine as a yellow oil, MS: 524 (M+H)+.

後処理

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customthe solvent was evaporated
  3. customThe crude material obtained
  4. temperaturerefluxed for 6 hrs
  5. dry with materialDistribution between a diluted aqueous solution of NaOH and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent

出典と根拠

ORDレコード
ord-bc02f105596b495b8b159f12935ce4ed
出典データセット
uspto-grants-2007_08
特許番号
US07253282B2

反応ノート

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