Tetrahydrofuran → (R)-3-(methoxyacetylamino)-1-phenylmethylpiperidine

HRID 1614

反応式

HRID 1614 の反応式
O1CCCC1.[C:6]1([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([NH2:19])[CH2:14]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:27][O:28][CH2:29][C:30](Cl)=[O:31]>O.C(Cl)Cl>[CH3:27][O:28][CH2:29][C:30]([NH:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][N:13]([CH2:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:14]1)=[O:31]

参加物

7

反応物 4

HCID 8028Tetrahydrofuran3 回HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 854130(3R)-1-benzylpiperidin-3-amine

生成物 1

HCID 51728477(R)-3-(methoxyacetylamino)-1-phenylmethylpiperidine収率 97%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a 50 ml anhydrous tetrahydrofuran solution of 5.00 g (26.3 mmol) of (R)-1-phenylmethyl-3-aminopiperidine (Referential example 7) in a 300 ml three-necked flask was added a 50 ml anhydrous tetrahydrofuran solution of 3.20 g (1.2 eg.) of triethylamine, and, to this reaction mixture was added dropwise a 50 ml anhydrous tetrahydrofuran solution of 2.85 g (1.0 eg.) of methoxyacetyl chloride under stirring and cooling with ice. After reacted for 5 hours at room temperature, methylene chloride and small amount of water were added to extract (20 ml×6). The organic layers were combined and dried over anhydrous sodium sulfate. Then, solvent was distilled off under reduced pressure and the residue thus obtained was purified by column chromatography (alumina, ethyl acetate:n-hexane=1:1) to obtain 6.67 g (yield 97 %) of title compound as a pale yellow oil.

後処理

  1. temperaturecooling with ice
  2. customAfter reacted for 5 hours at room temperature
  3. extractionto extract (20 ml×6)
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, solvent was distilled off under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by column chromatography (alumina, ethyl acetate:n-hexane=1:1)

出典と根拠

ORDレコード
ord-44351331f59d49308273d55a1a4782d5
出典データセット
uspto-grants-1998_03
特許番号
US05726188

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