Aluminium lithium hydride → (S)-tert-butyl 1-cyclobutyl-3-oxopropan-2-ylcarbamate

HRID 1511453ノート

反応式

HRID 1511453 の反応式
[CH:1]1([CH2:5][C@H:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:7](N(OC)C)=[O:8])[CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([CH2:5][C@H:6]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:7]=[O:8])[CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57893099(S)-tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate

生成物 1

HCID 57893126(S)-tert-butyl 1-cyclobutyl-3-oxopropan-2-ylcarbamate収率 86.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of (S)-tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (4.3 g, 15 mmol) in anhydrous tetrahydrofuran (100 mL) under argon at −78° C., was slowly added lithium aluminum hydride (1M in tetrahydrofuran, 15 mL, 15 mmol). After 2 hours, the reaction mixture was quenched by slowly adding 1N HCl (15 mL) and the reaction mixture was warmed up to room temperature after the addition was complete. The reaction mixture was diluted with ethyl acetate (500 mL), washed with 1N HCl, water, then brine, and dried over magnesium sulfate. Removal of the solvents under reduced pressure gave (S)-tert-butyl 1-cyclobutyl-3-oxopropan-2-ylcarbamate (2.95 g) as an oil.

後処理

  1. customat −78° C.
  2. customthe reaction mixture was quenched
  3. additionby slowly adding 1N HCl (15 mL)
  4. additionafter the addition
  5. additionThe reaction mixture was diluted with ethyl acetate (500 mL)
  6. washwashed with 1N HCl, water
  7. dry with materialbrine, and dried over magnesium sulfate
  8. customRemoval of the solvents under reduced pressure

出典と根拠

ORDレコード
ord-d6363400e8734a58bd69e737206959b3
出典データセット
uspto-grants-2012_07
特許番号
US08211897B2

反応ノート

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