4-Methylmorpholine → Ethyl (+/-)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate

HRID 989899ノート

反応式

HRID 989899 の反応式
[C:1]([C:4]1[N:5]=[C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][CH:8]=1)(O)=[O:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.CO>[OH:2][CH2:1][C:4]1[N:5]=[C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:7][CH:8]=1

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11220404HCID 11220404、化合物

生成物 1

HCID 23389065Ethyl (+/-)-4-(4-hydroxymethyl-1,3-oxazol-2-yl)-3-phenylbutanoate収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl (±)-4-(4-carboxy-1,3-oxazol-2-yl)-3-phenylbutanoate (500 mg, 1.65 mmole) in dry THF (8 mL) was added 4-methylmorpholine (0.22 mL, 1.99 mmole) then ethyl chloroformate (0.19 mL, 1.99 mmole) at 0° C. After 10 min, NaBH4 (249 mg, 6.59 mmole) was added all at once, then MeOH (8 mL) was added dropwise. After 30 min, the mixture was quenched with H2O (20 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel (80% EtOAc/hexanes) to give the title compound (371 mg, 78%) as a yellow oil: MS (ES) m/e 290 (M+H)+.

後処理

  1. customat 0° C
  2. additionwas added dropwise
  3. waitAfter 30 min
  4. customthe mixture was quenched with H2O (20 mL)
  5. extractionextracted with EtOAc (3×20 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on silica gel (80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-a10f23b0051d445689eb613a346e7c68
出典データセット
uspto-grants-2002_10
特許番号
US06458814B1

反応ノート

読み込み中…