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

HRID 989899노트

반응식

HRID 989899 반응식
[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

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 11220404HCID 11220404, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a10f23b0051d445689eb613a346e7c68
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458814B1

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