Lithium borohydride → [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1040461ノート

反応式

HRID 1040461 の反応式
C[O:2][C:3](=O)[CH:4]([NH:11][C:12](=[O:23])[C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[Li+].[BH4-]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:13]([C:12](=[O:23])[NH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:3][OH:2])[CH3:14])([CH3:20])([CH3:21])[CH3:22]

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 67390971HCID 67390971、化合物

生成物 1

HCID 67389928[(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of ((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyridin-2-yl-acetic acid methyl ester (1.12 g, 3.32 mmol) in 15 mL of THF was added LiBH4 (2 M in THF, 1.66 mL, 3.32 mmol) drop wise and the reaction was stirred at room temperature for 16 h. The reaction was carefully quenched by water, neutralized with 0.1 N HCl aq., extracted with EtOAc, washed with aq. NaHCO3 and Brine. Dried over Na2SO4, filtered and concentrated in vacuo to afford [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (770 mg, 77%) as a white foam, m/z 310.60 [M+1]+

後処理

  1. customThe reaction was carefully quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with aq. NaHCO3 and Brine
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-68f4059682a540188aca634e6e09ed4f
出典データセット
uspto-grants-2013_10
特許番号
US08552205B2

反応ノート

読み込み中…