Aluminium lithium tri-tert-butoxide hydride → (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate

HRID 552795ノート

反応式

HRID 552795 の反応式
[C:1]([O:4][CH2:5][C:6](=[O:27])[C@@H:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:19]=[CH:18][C:12]2[O:13][C:14]([CH3:17])([CH3:16])[O:15][C:11]=2[CH:10]=1)(=[O:3])[CH3:2].[Li].CC([O-])(C)C.CC([O-])(C)C.CC([O-])(C)C.[Al+3]>C(O)C>[C:1]([O:4][CH2:5][C@@H:6]([OH:27])[C@@H:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:8][C:9]1[CH:19]=[CH:18][C:12]2[O:13][C:14]([CH3:16])([CH3:17])[O:15][C:11]=2[CH:10]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6328594Aluminium lithium tri-tert-butoxide hydrideHCID 67164867(S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate

生成物 1

HCID 67164253(2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate収率 101.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of (S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-oxobutyl acetate (3270 mg, 8311 μmol) in 100 mL of ethanol was cooled to −78° C. and added to a solution of lithium aluminum tri-tert-butoxyhydride (16623 μl, 16623 μmol) in 45 mL of ethanol at −78 C dropwise via a cannula over 10 minutes. After stirring at −78° C. for 2 hours the reaction was quenched with 25 mL of 1 N HCl and diluted with ethyl acetate (500 mL). The mixture was poured into 200 mL of water, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organics were washed with water, brine, and dried over sodium sulfate and concentrated to provide (2S,3S)-3-(tert-butoxycarbonyl)-4-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-hydroxybutyl acetate (3220 mg, 98% yield) as a white solid.

後処理

  1. customwas quenched with 25 mL of 1 N HCl
  2. additiondiluted with ethyl acetate (500 mL)
  3. additionThe mixture was poured into 200 mL of water
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  6. washThe combined organics were washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-240880fd5eaa404d83d63e841bdcb9e5
出典データセット
uspto-grants-2011_05
特許番号
US07951838B2

反応ノート

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