Triethylamine → (S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate

HRID 2208979ノート

反応式

HRID 2208979 の反応式
[OH:1][C@H:2]([C@H:4]1[CH2:8][N:7]([C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:6](=[O:17])[CH2:5]1)[CH3:3].C1([C@H](N)C)C=CC=CC=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:1][C@H:2]([C@@H:4]1[CH2:5][C:6](=[O:17])[N:7]([C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:8]1)[CH3:3])(=[O:37])=[O:36]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6431891-Phenethylamine, (+)-HCID 58072048(R)-4-((S)-1-hydroxyethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one

生成物 1

HCID 117843588(S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of (R)-4-((S)-1-hydroxyethyl)-1-((R)-1-phenylethyl)pyrrolidin-2-one 1.16 (prepared in an analogous fashion to Example 1.05, but starting the sequence with (R)-1-phenylethanamine in place of (R)-1-(4-methoxyphenyl)ethanamine) (300 mg, 1.28 mmol) in DCM (6 mL) was added triethylamine (0.25 mL, 1.8 mmol) and the reaction mixture was cooled to 0° C. Then methanesulfonyl chloride (0.11 mL, 1.4 mmol) was added and stirred at the same temperature for 30 min. The reaction mixture was then diluted with DCM and washed successively with 1N HCl, brine and dried over anhydrous magnesium sulfate. The residue was purified by flash column chromatography (SiO2, 80% EtOAc/hexanes to 100% EtOAc) to give (S)-1-((R)-5-oxo-1-((R)-1-phenylethyl)pyrrolidin-3-yl)ethyl methanesulfonate 1.17.

後処理

  1. washwashed successively with 1N HCl, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue was purified by flash column chromatography (SiO2, 80% EtOAc/hexanes to 100% EtOAc)

出典と根拠

ORDレコード
ord-6b695bb05b41473a81f02755341712ec
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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