Methanol → (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoic acid

HRID 2269350ノート

反応式

HRID 2269350 の反応式
[OH:1][C@H:2]([CH3:21])[C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].CO>C1COCC1.O>[OH:1][C@H:2]([CH3:21])[C@@H:3]([CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)[C:4]([OH:6])=[O:5]

参加物

6

反応物 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrate3 回HCID 57272933Methyl (2R,3R)-3-Hydroxy-2-(4-phenylcyclohexylmethyl)butanoate

生成物 1

HCID 57301164(2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoic acid収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

A mixture of methyl (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoate (4.17 g, 0.014 mol) and lithium hydroxide monohydrate (0.59 g, 0.014 mol) is stirred at 25° C. in a mixture of THF (30 mL), methanol (15 mL) and water (15 mL) for 72 h. The reaction is not complete and an additional 0.88 g (0.021 mol) of lithium hydroxide monohydrate in water (10 mL) is added. After 6 h an additional 0.59 g (0.014 mol) of solid lithium hydroxide monohydrate and the mixture is stirred at 25° C. for 18 h. The mixture is concentrated in vacuo and the residue is taken up in water, chilled in an ice-bath and the pH is adjusted to 2 with sodium bisulfate. The mixture is extracted with dichloromethane. The combined extracts were washed with saturated sodium chloride, dried over sodium sulfate and concentrated in vacuo to give 3.43 g (89%) of (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoic acid as a yellow solid.

後処理

  1. concentrationThe mixture is concentrated in vacuo
  2. temperaturechilled in an ice-bath
  3. extractionThe mixture is extracted with dichloromethane
  4. washThe combined extracts were washed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a3968a2575be41d6a32bf969b4a23bf1
出典データセット
uspto-grants-2001_12
特許番号
US06329400B1

反応ノート

読み込み中…