Triethylamine → (2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate

HRID 631762ノート

反応式

HRID 631762 の反応式
[OH:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[Br:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20](Cl)=[O:21]>ClCCCl.O>[Br:18][CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20]([O:1][C@@H:2]([CH3:10])[C:3](=[O:4])[N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:21]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanoneHCID 12575778Bromo-4-chlorophenylacetyl chloride

生成物 1

HCID 42644107(2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate収率 59%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

実験手順

To a solution of (2S)-2-hydroxy-1-(pyrrolidin-1-yl)propan-1-one (24.0 g, 0.17 mol) in DCE (120 mL) was added triethylamine (84.69 g, 0.84 mol) and 2-bromo-2-(4-chlorophenyl)acetyl chloride (crude, 46.29 g, 0.17 mol) at 0° C. The reaction mixture was stirred for 2 h at RT. The reaction mixture was diluted with water (200 mL) and separated the organic layer. The organic layer was washed with 10% NaS2O3 (100 mL) and saturated sodium bicarbonate (60 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude residue was purified by flash column on 100-200 mesh silica-gel (20-25% ethyl acetate-hexane) to afford (2S)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-bromo-2-(4-chlorophenyl)acetate 4 (37.5 g, 59%) as brown sticky gum.

後処理

  1. customseparated the organic layer
  2. washThe organic layer was washed with 10% NaS2O3 (100 mL) and saturated sodium bicarbonate (60 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by flash column on 100-200 mesh silica-gel (20-25% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-acf81ffc1af64838a48ecd215fbe61ec
出典データセット
uspto-grants-2016_04
特許番号
US09321716B1

反応ノート

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