Boc-D-alanine methyl ester → tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate

HRID 588505ノート

反応式

HRID 588505 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:14])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[O:11]=[CH:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:14]

参加物

4

反応物 2

HCID 637612Boc-D-alanine methyl esterHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 10910049tert-butyl N-((2R)-1-oxopropan-2-yl)carbamate収率 165%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a cooled solution of (R)-methyl 2-(tert-butoxycarbonylamino)propanoate (40.0 g, 98.0 mmol) in DCM (200 mL) at −78° C. was added diisobutylaluminium hydride (208 mL, 1.0 M in THF) dropwise over 30 min. The reaction mixture was stirred at −78° C. for 1.5 h then quenched with water (50 mL). After warmed to rt, the white precipitate was removed by filtration over Celite. The organic layer was then washed with brine, dried (Na2SO4), and concentrated. The crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1) to give (R)-tert-butyl 1-oxopropan-2-ylcarbamate (28.0 g, 82%). 1H NMR (DMSO-d6, 400 MHz) δ 9.43 (s, 1H), 7.33 (d, J=6.0 Hz, 1H), 3.85 (m, 1H), 1.39 (s, 9H), 1.12 (d, J=7.2 Hz, 3H).

後処理

  1. customthen quenched with water (50 mL)
  2. temperatureAfter warmed to rt
  3. customthe white precipitate was removed by filtration over Celite
  4. washThe organic layer was then washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography (petroleum ether: EtOAc, 10:1)

出典と根拠

ORDレコード
ord-f5f8e139b102483f932dbe840df1845b
出典データセット
uspto-grants-2016_01
特許番号
US09227951B2

反応ノート

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