Acetic Acid → HCID 68315199、化合物

HRID 333215ノート

反応式

HRID 333215 の反応式
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1([F:23])[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>CN(C)C=O.O>[F:15][C:16]1([F:23])[CH2:21][CH2:20][CH:19]([N:11]2[CH2:12][CH2:13][CH:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10]2)[CH2:18][CH2:17]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 7238334-(N-Boc-amino)piperidineHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 157890924,4-Difluorocyclohexanone

生成物 1

HCID 68315199HCID 68315199、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (2.00 g, 10 mmol) and 4,4-difluorocyclohexanone (1.61 g, 12 mmol) in N,N-dimethylformamide (50 mL), kept at room temperature, acetic acid (3 mL, 50 mmol) and tetramethylammonium triacetoxyborohydride (5.24 g, 20 mmol) were subsequently added. The reaction mixture was allowed to stir overnight then diluted with water (150 mL), extracted with diethyl ether and the organic layer was discarded. The aqueous phase was made basic with ammonia and extracted with ethyl acetate (3×100 mL). The combined organic phases were dried over sodium sulfate, evaporated to dryness and the residue was purified by column chromatography, using dichloromethane/ethanol/concentrated aqueous ammonia: 97.5/2.5/0.25 as the mobile phase. Tert-butyl [1-(4,4-difluorocyclohexyl)-piperidin-4-yl]-carbamate was obtained in fairly good yield as a white solid (2.5 g, 78%).

後処理

  1. customkept at room temperature
  2. extractionextracted with diethyl ether
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customevaporated to dryness
  6. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-c74ef471dfc5466b94b44df384896de4
出典データセット
uspto-grants-2014_11
特許番号
US08877944B2

反応ノート

読み込み中…