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

HRID 2220929Notes

Reaction equation

HRID 2220929 reaction equation
[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

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 129701552-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3ee7de965d264f8bbb4a2c00ec0d8899
Source dataset
uspto-grants-2008_05
Patent number
US07368455B2

Reaction notes

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