Methyl iodide → 3-(3-Chloro-2-fluorophenyl)-1-methylpyrrolidin-3-ol

HRID 1931844ノート

反応式

HRID 1931844 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[F:21])([OH:13])[CH2:9]1)C1C=CC=CC=1.IC.N1CCOCC1>CN(C)C=O>[Cl:20][C:16]1[C:15]([F:21])=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][N:8]([CH3:1])[CH2:9]2)[CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 8083MorpholineHCID 685157901-Benzyl-3-(3-chloro-2-fluorophenyl)pyrrolidin-3-ol

生成物 1

HCID 251436693-(3-Chloro-2-fluorophenyl)-1-methylpyrrolidin-3-ol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Preparation according to Example 34: (+)-1-benzyl-3-(3-chloro-2-fluorophenyl)-pyrrolidin-3-ol (0.93 g, 3.05 mmol) and iodomethane (1 mL, 15.9 mmol), dimethyl formamid (3 mL), morpholine (2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.289 g. [α]D=+25.9° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether: M.p. 123-125° C.; MS m/z (relative intensity, 70 eV) 229 (M+, 7), 157 (8), 129 (6), 58 (29), 57 (bp).

後処理

  1. customPreparation
  2. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1)
  3. customrecrystallized from methanol/diethyl ether/diisopropyl ether

出典と根拠

ORDレコード
ord-eaee7de016e94cc0a654796285c37854
出典データセット
uspto-grants-2012_05
特許番号
US08188301B2

反応ノート

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