Lithium Hydroxide → [4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid

HRID 713432

反応式

HRID 713432 の反応式
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)C.[Li+].[OH-].[Li+].[Cl-]>C1COCC1.CO>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:21])=[O:3])[CH2:7][CH2:8]2)=[O:20])=[CH:14][CH:15]=1

参加物

6

反応物 3

HCID 3939Lithium HydroxideHCID 433294Lithium ChlorideHCID 71226965[4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

生成物 1

HCID 71227333[4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid収率 155.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a stirred solution of [4-(4-chloro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (1.0 g, 3.03 mmol) in 12 mL of THF and 4 mL of MeOH, was added LiOH (0.39 g, 16.14 mmol in 3 mL of water). After 3 h at ambient temperature the solvent was removed in vacuo, then diluted with 20 mL of water (pH 14). The residue was treated with 12 mL of 1 N HCl (pH 4), frozen at −78° C. then lyophilized for 24 hours to yield the title product (1.33 g, 4.70 mmol, >99% yield) with LiCl salt. MS (ESI) m/z 282.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.26 min.

後処理

  1. customAfter 3 h at ambient temperature the solvent was removed in vacuo
  2. additiondiluted with 20 mL of water (pH 14)
  3. additionThe residue was treated with 12 mL of 1 N HCl (pH 4)

出典と根拠

ORDレコード
ord-c7879bfb1af145ed91ad2becf2310cbf
出典データセット
uspto-grants-2015_11
特許番号
US09181266B2

関連ノート

読み込み中…