Cyanogen Bromide → (S)-1-(4-Bromo-2-butynyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone

HRID 1079030ノート

反応式

HRID 1079030 の反応式
C(N(CC)[CH2:4][C:5]#[C:6][CH2:7][N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:9]1=[O:21])C.N#C[Br:26]>C(OCC)C>[Br:26][CH2:4][C:5]#[C:6][CH2:7][N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:9]1=[O:21]

参加物

4

反応物 2

HCID 10476Cyanogen BromideHCID 53818580(S)-1-[4-diethylamino-2-butynyl]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone

生成物 1

HCID 54240231(S)-1-(4-Bromo-2-butynyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone収率 81.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of 2.4 g of (S)-1-[4-diethylamino-2-butynyl]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone and 0.8 g of cyanogen bromide in 40 ml of diethyl ether is stirred at room temperature for 18 hours. The solution is washed with 30 ml of 1N hydrochloric acid and saturated sodium bicarbonate, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, methylene chloride) to give 2.0 g of the desired product as a colorless oil. [α]D26 =-31° (methylene chloride).

後処理

  1. washThe solution is washed with 30 ml of 1N hydrochloric acid and saturated sodium bicarbonate
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by chromatography (silica gel, methylene chloride)

出典と根拠

ORDレコード
ord-c7ca2749abe546448987a90318b82987
出典データセット
uspto-grants-1996_08
特許番号
US05550257

反応ノート

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