Borane → HCID 14821719、化合物

HRID 325245ノート

反応式

HRID 325245 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:13][C@H:9]1[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 6331BoraneHCID 11860409Boc-Hyp(Bzl)-OH

生成物 1

HCID 14821719HCID 14821719、化合物収率 100.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of trans-N-t-butoxycarbonyl-4-benzyloxy-L-proline (3.32 g, 10.3 mmol) in 20 mL of THF was cooled in an ice/acetone bath and a solution of borane in THF (1M, 20.6 mL, 20.6 mrnmol) was added dropwise. The solution was stirred for 2 hours then the cooling bath was removed and the mixture stirred overnight. The reaction was quenched by the careful addition of water followed by the addition of 20 mL of 1N aqueous HCl and then poured into ethyl acetate. The layers were separated and the aqueous layer extracted with 2 portions of ethyl acetate. The combined organic extracts were 2M aqueous sodium carbonate, water and brine, dried, filtered and concentrated to provide 3.19 g (100%) of the title compound. MS (DCI, NH3): 308 (MH+).

後処理

  1. customthe cooling bath was removed
  2. stirringthe mixture stirred overnight
  3. customThe reaction was quenched by the careful addition of water
  4. additionfollowed by the addition of 20 mL of 1N aqueous HCl
  5. additionpoured into ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with 2 portions of ethyl acetate
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-76e30c9d64dc4ce09797782144fc8da9
出典データセット
uspto-grants-2001_04
特許番号
US06221865B1

反応ノート

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