4-Methylmorpholine → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

HRID 277677ノート

反応式

HRID 277677 の反応式
[C:1]([NH:8][C@H:9]([C:13](O)=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[NH:8]([C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[C@H:9]([CH2:13][OH:14])[CH:10]([CH3:11])[CH3:12]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 83693Boc-L-ValineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

生成物 1

HCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To 5 g (0.023 mol) of Boc-Valine dissolved in THF (30 mL) at −10° C. under N2 are added NMM (2.5 mL 0.023 mol) and IBCF (3 mL, 0.023 mol). The reaction mixture is stirred 15 minutes and filtered. The filtrate is added slowly to an ice-cold solution of NaBH4 (2.3 g, 0.061 mol) in H2O (10 mL) and stirred 1 hour at ice-bath temperature then 1 hour at room temperature. The reaction mixture is cooled to 0° C. and treated with saturated NaHCO3 solution, extracted with EtOAc, washed with 1M HCl saturated with NaHCO3, dried over anhydrous MgSO4, and evaporated to dryness. The crude Boc-ValCH2OH product is purified over a silica gel column eluted with 95:5 EtOAc/MeOH.

後処理

  1. filtrationfiltered
  2. stirringstirred 1 hour at ice-bath temperature
  3. custom1 hour
  4. customat room temperature
  5. extractionextracted with EtOAc
  6. washwashed with 1M HCl saturated with NaHCO3
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated to dryness
  9. customThe crude Boc-ValCH2OH product is purified over a silica gel column
  10. washeluted with 95:5 EtOAc/MeOH

出典と根拠

ORDレコード
ord-fa916a9574a14c058340cd4147ce6fb7
出典データセット
uspto-grants-2002_03
特許番号
US06358928B1

反応ノート

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