Acetic Anhydride → HCID 67025604, compound

HRID 1951076Notes

Reaction equation

HRID 1951076 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([N:15]1[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH:17]([NH2:28])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[CH2:8]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C@H:17]([NH:28][C:5](=[O:7])[CH3:6])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 672341221-Benzyl-4-(3,4-dichlorophenyl)pyrrolidin-3-amine

Product 1

HCID 67025604HCID 67025604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of acetic anhydride (0.75 ml, 7.97 mmol) in THF (10 ml) was added a solution of rac-(3S,4R)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-ylamine (described herein above) (2.00 g, 6.22 mmol) in THF (10 ml) dropwise over 30 minutes. The reaction mixture was stirred one additional hour, concentrated under vacuo, taken up in EtOAc, washed with aq. NaHCO3. and then the organic phase was dried over Na2SO4 to afford the intermediate N-[(3S,4R)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-acetamide. To this intermediate in THF (10 ml) at 0° C., was added portion wise LiAlH4 (0.49 g, 12.83 mmol). Stirring was continued over night at 65° C.). The reaction mixture was then heated at 65° C. over night, cooled to RT and carefully quenched with aq. NaHCO3. The product was extracted several times with EtOAc, the organic phases were then dried over Na2SO4 and the product purified by flash chromatography (SiO2, CH2Cl2/MeOH 9:1) to afford 1.03 g (46%) of rac-[(3S,4R)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-amine as a colorless oil. ES-MS m/e: 349.10 (M+H+).

Workup

  1. customdropwise over 30 minutes
  2. concentrationconcentrated under vacuo
  3. washwashed with aq. NaHCO3
  4. dry with materialand then the organic phase was dried over Na2SO4

Sources & evidence

ORD record
ord-441eb4e7d2b64b60bb2f4a05df74db19
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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