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Lithium Hydroxide → (S)-4-(4-((4'-Chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid

HRID 1771201
ノート
印刷プレビュー

反応式

HRID 1771201 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@@H:14]([OH:32])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C@@H:14]([OH:32])[CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH2:17][CH2:16]2)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 56650672(S)-Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate2 回

生成物 1

HCID 58080142(S)-4-(4-((4'-Chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

(S)-Ethyl 4-(4-((4′-chlorobiphenyl-2-yl)(hydroxy)methyl)piperidin-1-yl)benzoate (INTERMEDIATE 11B, 150.0 mg, 0.33 mmol) was dissolved in THF (6.0 ml) and methanol (1.4 ml). A solution of LiOH (40.6 mg) in water (1.4 ml) was added. The solution was heated at 500 overnight. The reaction mixture was allowed to cool to room temperature and then concentrated under reduced pressure. The residue was diluted with water (5 ml), acidified with 1N aq. HCl (2.0 ml), and extracted with DCM (2×5 ml). The extract was dried (MgSO4), filtered through cotton, and evaporated under vacuum to provide the title product as a substantially separated enantiomer (155 mg, yield: almost quantitative) 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 0.79-0.94 (m, 1H) 0.98-1.12 (m, 1H) 1.14-1.40 (m, 4H) 2.04 (m, 1H) 2.67 (td, J=12.51, 2.78 Hz, 1H) 2.78 (td, 1H) 3.74 (d, 1H) 3.91 (m, 1H) 4.48 (d, 1H) 6.81 (d, 2H) 7.17-7.29 (m, 3H) 7.31-7.49 (m, 4H) 7.61 (dd, 1H) 7.84-7.93 (m, 2H).

後処理

  1. temperatureThe solution was heated at 500 overnight
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (5 ml)
  4. extractionextracted with DCM (2×5 ml)
  5. dry with materialThe extract was dried (MgSO4)
  6. filtrationfiltered through cotton
  7. customevaporated under vacuum

出典と根拠

ORDレコード
ord-13a72434d4ac44f38f4a79a7ed1e058e
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09248140B2

反応ノート

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