Acetic Acid → 2-[2-(4-Fluorophenyl)acetyl]4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester

HRID 22669노트

반응식

HRID 22669 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=O)[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O.Cl>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2회HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 129701552-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 207247462-[2-(4-Fluorophenyl)acetyl]4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (0.14 g, 0.4 mmol) and morpholine (0.038 mL, 0.43 mmol) in THF at room temperature is added Na(OAc)3BH (0.125 g, 0.6 mmol) and HOAc (0.022 mL, 0.4 mmol). The solution is stirred 12 hours then partitioned between diethyl ether and NaHCO3. The aqueous layer was extracted several times with ether and the organic layers combined, dried, and concentrated in vacuo to a clear oil which was re-dissolved in ether and one equivalent of ethereal HCl is added and a white solid forms. The solid is collected by filtration and 100 mg (60% yield) of the desired product is isolated as the HCl salt.

후처리

  1. customthen partitioned between diethyl ether and NaHCO3
  2. extractionThe aqueous layer was extracted several times with ether
  3. customdried
  4. concentrationconcentrated in vacuo to a clear oil which
  5. dissolutionwas re-dissolved in ether
  6. filtrationThe solid is collected by filtration

출처 및 근거

ORD 기록
ord-a7d95eb773b94f3aa041f7fac1c7466e
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849627B2

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