HCID 57803338, compound → HCID 60054959, compound

HRID 2367029Notes

Reaction equation

HRID 2367029 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[C@H:11]([C:24]([CH3:26])=[CH2:25])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH2:1]([O:8][C@H:9]1[CH2:13][NH:12][C@H:11]([CH:24]([CH3:26])[CH3:25])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57803338HCID 57803338, compound

Product 1

HCID 60054959HCID 60054959, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl (2S,4R)-4-(benzyloxy)-2-isopropenylpyrrolidine-1-carboxylate (1.00 g, 2.84 mmol) was dissolved in ethanol (40 mL) and then 5% Pd—C (100 mg) was added to the solution. The flask was purged with hydrogen and then shaken on a Parr under 53 psi atmosphere of hydrogen for 17 hours. The reaction was then flushed with nitrogen and filtered through Celite on a glass frit and washed with methanol. The filtrate was concentrated and chromatographed on silica gel (1% triethylamine/10% methanol/89% ethyl acetate) to furnish the amine as a pale yellow oil, 0.53 g (85%). LC/MS (M+H)+ m/z=220.2; 1H NMR (CDCl3) 7.33 (m, 5H), 4.49 (m, 2H), 4.12 (m, 1H), 3.19 (dd, 1H), 3.00 (m, 2H), 2.05 (m, 1H), 1.96 (bs, 1H), 1.49 (m, 2H), 1.00 (d, 3H), 0.91 (d, 3H).

Workup

  1. customThe flask was purged with hydrogen
  2. customThe reaction was then flushed with nitrogen
  3. filtrationfiltered through Celite on a glass frit
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel (1% triethylamine/10% methanol/89% ethyl acetate)

Sources & evidence

ORD record
ord-0aba6758fce045c99804f620e1aa53e6
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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