Methyl iodide → 3-(3-Chloro-5-fluorophenyl)-1-methylpyrrolidin-3-ol

HRID 1931852ノート

反応式

HRID 1931852 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)([OH:13])[CH2:9]1)C1C=CC=CC=1.IC.N1CCOCC1>CN(C)C=O>[Cl:21][C:16]1[CH:15]=[C:14]([C:10]2([OH:13])[CH2:11][CH2:12][N:8]([CH3:1])[CH2:9]2)[CH:19]=[C:18]([F:20])[CH:17]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 8083MorpholineHCID 685158581-Benzyl-3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol

生成物 1

HCID 251438123-(3-Chloro-5-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-5-fluorophenyl)-pyrrolidin-3-ol (0.1 g, 0.33 mmol) and iodomethane (1 mL, 15.9 mmol), dimethyl formamid (2 mL), morpholine (2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.05 g. [α]D=+21° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 114-115° C.; MS m/z (relative intensity, 70 eV) 229 (M+, 7), 129 (9), 109 (7), 58 (30), 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 ethanol/diethyl ether/diisopropyl ether

出典と根拠

ORDレコード
ord-7b15904429be4a78b123001c3d11d73e
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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