Borane → HCID 178502739、化合物

HRID 271350ノート

反応式

HRID 271350 の反応式
[CH3:1][O:2][N:3]([CH3:14])[C:4]([C@@H:6]1[CH2:9][C@H:8]([CH2:10][C:11](O)=[O:12])[CH2:7]1)=[O:5].B>C1COCC1>[CH3:1][O:2][N:3]([CH3:14])[C:4]([C@H:6]1[CH2:9][C@@H:8]([CH2:10][CH2:11][OH:12])[CH2:7]1)=[O:5]

参加物

4

反応物 2

HCID 6331BoraneHCID 178502740HCID 178502740、化合物

生成物 1

HCID 178502739HCID 178502739、化合物収率 64.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice cold solution of 3.0 g of cis-[3-(methoxy-methyl-carbamoyl)-cyclobutyl]-acetic acid in 50 mL of THF was added 15 mL of 1M borane in THF. The mixture was allowed to stir for 15 min in the cold, then warm and stir for 30 min. The reaction was quenched with 25 mL of 10% HCl and extracted into 3×50 mL of ethyl acetate. The combined extracts were diluted with 50 mL of toluene, dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum overnight gave 1.8 g of product as a colorless oil: MS (m+1)=188.45; 1H NMR (400 MHz, CDCl3) 3.62 (s, 3H), 3.6 (t, 2H), 3.18 (s, 3H), 2.35 (m, 1H), 2.3 (m, 3H), 1.984 (dd, 2H), 1.65 (dd, 2H).

後処理

  1. temperaturethen warm
  2. stirringstir for 30 min
  3. customThe reaction was quenched with 25 mL of 10% HCl
  4. extractionextracted into 3×50 mL of ethyl acetate
  5. additionThe combined extracts were diluted with 50 mL of toluene
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customDrying under vacuum overnight

出典と根拠

ORDレコード
ord-8b95acd2aab540b89b2dfb00caae9076
出典データセット
uspto-grants-2008_11
特許番号
US07452893B2

反応ノート

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