Chlorotrimethylsilane → beta-Amino-3-chlorobenzeneethanol

HRID 1911537ノート

反応式

HRID 1911537 の反応式
[BH4-].[Li+].Cl[Si](C)(C)C.[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[C:10](O)=[O:11]>C1COCC1>[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[CH2:10][OH:11]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 2907302-Amino-2-(3-chlorophenyl)acetic acidHCID 4148881Lithium borohydride

生成物 1

HCID 10953980beta-Amino-3-chlorobenzeneethanol収率 99.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of lithium borohydride in THF (10.5 ml, 2 M solution) under an argon atmosphere was added dropwise chlorotrimethylsilane (5.34 ml). The resulting suspension was cooled to 0° C. and amino-(3-chlorophenyl)-acetic acid (2.0 g) was added portionwise. The ice bath was removed and stirring at r.t. was then continued for 16 h. The mixture was quenched by dropwise addition of methanol (15 ml) and then concentrated in vacuo. The residue was suspended in ethyl acetate and washed with 2 N aq NaOH. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo to afford (RS)-2-amino-2-(3-chloro-phenyl)-ethanol (1.84 g, quant.) as a yellow viscous oil. MS (ISP): 174.2 ([{37Cl}M+H]+), 172.2 ([{35Cl}M+H]+).

後処理

  1. customThe ice bath was removed
  2. customThe mixture was quenched by dropwise addition of methanol (15 ml)
  3. concentrationconcentrated in vacuo
  4. washwashed with 2 N aq NaOH
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f8fe01c88dce4940b5387a139f0f98a5
出典データセット
uspto-grants-2013_12
特許番号
US08604061B2

反応ノート

読み込み中…