Nitrogen → HCID 59382877、化合物

HRID 2355402ノート

反応式

HRID 2355402 の反応式
N#N.[F:3][C:4]([F:21])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].C(=O)=O.CC(C)=O.[CH3:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][Mg]Cl.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[F:21][C:4]([F:3])([F:20])[C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:8]1)([OH:6])[CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH3:29]

参加物

8

反応物 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 49759206tert-Butyl 3-(trifluoroacetyl)piperidine-1-carboxylateHCID 178495008HCID 178495008、化合物

生成物 1

HCID 59382877HCID 59382877、化合物収率 15%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under protection of N2 gas, tert-butyl 3-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate (102 mg, 0.363 mmol) was dissolved dry THF (8 mL) and cooled to −78° C. (dry ice/acetone bath). 1.22 M methoxybutylmagnesium chloride in THF (600 μL, 2 equiv) solution was added slowly. After 10 min, the reaction was allowed to warm up to rt slowly. After 2 h, satd aq NH4Cl (15 mL) solution was added to the reaction mixture. The mixture was diluted with diethyl ether and the layers were separated. The aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. After concentration, the crude product was purified by prep HPLC to afford tert-butyl 3-(1,1,1-trifluoro-2-hydroxy-6-methoxyhexan-2-yl)piperidine-1-carboxylate (20 mg, 15%).

後処理

  1. waitAfter 2 h
  2. additionwas added to the reaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with diethyl ether (3×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by prep HPLC

出典と根拠

ORDレコード
ord-27ce670f38404cc38dc2dbf48b09ca42
出典データセット
uspto-grants-2010_07
特許番号
US07754737B2

反応ノート

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