Lithium borohydride → Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

HRID 1504838ノート

反応式

HRID 1504838 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14](OC)=[O:15])[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1.[Cl-].[NH4+]>[OH:15][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11][S:12][CH3:13]

参加物

5

反応物 2

HCID 4148881Lithium borohydrideHCID 11097398(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoate

生成物 1

HCID 11356792Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of methyl N-(tert-butoxycarbonyl)methioninate (47.7 g, 0.181 mol) in THF (500 mL) was added lithium borohydride (16.0 g, 0.734 mol) at 0° C. The reaction mixture was allowed to warm to room temperature. After 2 hours, the reaction mixture was diluted with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H22NO3S [M+H]+ 236. found 236. 1H NMR (400 MHz, CD3OD) δ 3.68-3.64 (m, 1H), 3.54-3.47 (m, 2H), 2.59-2.48 (m, 2H), 2.10 (s, 3H), 1.88-1.64 (m, 2H), 1.49 (s, 9H).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-55297eb4a0e54e548b67bcb026d6c517
出典データセット
uspto-grants-2015_12
特許番号
US09216173B2

反応ノート

読み込み中…