Isopropanol → HCID 59441798, compound

HRID 1014239Notes

Reaction equation

HRID 1014239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[N+:14]([O-])=O.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(C)C>C(O)C.[Pd]>[NH2:14][C:4]1[CH:5]=[C:6]([O:9][CH2:10][C@@H:11]([OH:12])[CH2:13][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 31268PyrrolidineHCID 59441631HCID 59441631, compound

Product 1

HCID 59441798HCID 59441798, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

In a sealed tube were placed (2S)-2-({[4-(methyloxy)-3-nitrophenyl]oxy}methyl)oxirane (1.0 g, 4.4 mmol), pyrrolidine (3.2 g, 44 mmol), and isopropanol (20 mL). The mixture was heated under microwave to 140° C. for 10 min. Removal of the isopropanol afforded the crude product which was placed in ethanol (100 mL) with 10% palladium on carbon (0.5 g). The reation mixture was kept stirring under H2 at 60 psi overnight. Filtration removed the catalyst and concentration afforded (2S)-1-{[3-amino-4-(methyloxy)phenyl]oxy}-3-(1-pyrrolidinyl)-2-propanol (1.1 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.67 (ddd, J=6.4, 3.5, 3.3 Hz, 4H), 2.47-2.50 (m, 1 H), 2.55 (d, J=1.8 Hz, 4 H), 2.64 (dd, J=12.3, 5.7 Hz, 1 H), 3.63-3.71 (m, 4 H), 3.75-3.82 (m, 1 H), 3.83-3.89 (m, 1 H), 4.70 (s, 2 H), 4.88 (s, 1 H), 6.03 (dd, J=8.4, 2.9 Hz, 1 H), 6.24 (d, J=2.9 Hz, 1 H), 6.63 (d, J=8.8 Hz, 1 H).

Workup

  1. customIn a sealed tube were placed
  2. customRemoval of the isopropanol
  3. customafforded the crude product which
  4. filtrationFiltration
  5. customremoved
  6. concentrationthe catalyst and concentration

Sources & evidence

ORD record
ord-204a9cdd96c74e89b58f9594b4bb09f8
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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