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

HRID 277678ノート

反応式

HRID 277678 の反応式
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10](O)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN1CCOCC1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

生成物 1

HCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-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 5.7 g (0.023 mol) of Boc-PheOH 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 for 15 minutes and filtered. The filtrate is slowly added to an ice-cold solution of NaBH4 (2.3 g, 0.061 mol) in H2O (10 mL) and then stirred for 1 hour at ice-bath temperature followed by stirring for 1 hour at room temperature. The reaction is cooled to 0° C., treated with saturated NaHCO3 solution, extracted with EtOAc, washed with 1M HCl, washed with water, dried over anhydrous MgSO4, and evaporated to dryness. The crude product is purified over a silica gel column eluted with 95:5 EtOAc/MeOH.

後処理

  1. filtrationfiltered
  2. stirringstirred for 1 hour at ice-bath temperature
  3. stirringby stirring for 1 hour at room temperature
  4. extractionextracted with EtOAc
  5. washwashed with 1M HCl
  6. washwashed with water
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated to dryness
  9. customThe crude 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-ff64f4d6182e4e08be27bf3520af547f
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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