Pyrrolidine → HCID 59371462, compound

HRID 2095376Notes

Reaction equation

HRID 2095376 reaction equation
CO[C:3](=[O:30])[CH2:4][CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([O:17][CH2:18][C@@H:19]3[CH2:22][CH2:21][N:20]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:16]=2)[O:8][N:7]=1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[C:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][C@H:19]1[CH2:18][O:17][C:15]1[CH:16]=[C:11]([C:9]2[O:8][N:7]=[C:6]([CH2:5][CH2:4][C:3]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH:10]=2)[CH:12]=[N:13][CH:14]=1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 59371583HCID 59371583, compound

Product 1

HCID 59371462HCID 59371462, compoundYield 100.8%

Conditions

Temperature
100 °C

Procedure

To 3-[5-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-3-isoxazolyl]propionic acid methyl ester (210 mg, 0.5 mmol) was added pyrrolidine (1.2 mL, 15 mmol). The mixture was heated at 100° C. for 12 h, cooled, and concentrated. The residue was dissolved in water and extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by CC on SiO2 with EtOAc/hexane 1:1 to give 3-[5-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-3-isoxazolyl]-1-(1-pyrrolidinyl)-1-propanone (230 mg, 99%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by CC on SiO2 with EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-af41226fdf9f4b739e0f57181968b8ce
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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