Pentanal → benzyl N-[1-(2-fluoropentyl)piperidin-4-yl]carbamate

HRID 445989ノート

反応式

HRID 445989 の反応式
ClC(Cl)C(O)=O.CC1(C)N(C)[C:11](=O)[C@H:10]([CH2:15][C:16]2[CH:21]=CC=CC=2)N1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:33])(=O)=O)=CC=1.C(=O)CCCC.[NH:49]1[CH2:54][CH2:53][CH:52]([NH:55][C:56](=[O:65])[O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH2:51][CH2:50]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O.O1CCCC1.CC(O)C>[F:33][CH:10]([CH2:15][CH2:16][CH3:21])[CH2:11][N:49]1[CH2:50][CH2:51][CH:52]([NH:55][C:56](=[O:65])[O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH2:53][CH2:54]1

参加物

10

反応物 6

HCID 8063PentanalHCID 516892Sodium BicarbonateHCID 588007N-FluorobenzenesulfonimideHCID 15143044-Cbz-aminopiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 16217984Dichloroacetic acid--(5S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one (1/1)

生成物 1

HCID 71293837benzyl N-[1-(2-fluoropentyl)piperidin-4-yl]carbamate収率 52.7%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

(5S)-(−)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone dichloroacetic acid (90 mg, 0.259 mmol), N-fluorobenzenesulfonimide (484 mg, 1.53 mmol), 2-propanol (0.4 ml) and tetrahydrofuran (dehydrated) (3.6 ml) were mixed at room temperature. The reaction mixture was cooled to −10° C., and pentanal (0.175 ml, 1.67 mmol) was then added, followed by stirring for three hours and 20 minutes while naturally warming from −10° C. to room temperature. Benzyl N-(piperidin-4-yl)carbamate obtained in Example 1b (304 mg, 1.3 mmol) and sodium triacetoxyborohydride (600 mg, 2.83 mmol) were added to the reaction mixture, which was stirred at room temperature for 15 hours and 40 minutes. Water and an aqueous sodium bicarbonate solution were added to the reaction mixture, the insoluble matter was removed by filtration, and the resulting filtrate was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (silica gel, elution solvent: ethyl acetate/heptane) to give a chiral form mixture of the title compound (44 mg, yield 10.5%).

後処理

  1. temperaturewhile naturally warming from −10° C. to room temperature
  2. stirringwas stirred at room temperature for 15 hours and 40 minutes
  3. customthe insoluble matter was removed by filtration
  4. extractionthe resulting filtrate was extracted with ethyl acetate twice
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (silica gel, elution solvent: ethyl acetate/heptane)
  9. customto give

出典と根拠

ORDレコード
ord-2f5e004a321f49ac9fc654fd76b8df2c
出典データセット
uspto-grants-2013_07
特許番号
US08476301B2

反応ノート

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