D-Psicose → HCID 59420852, compound

HRID 499083Notes

Reaction equation

HRID 499083 reaction equation
[CH2:1]([O:3][C:4]([C:6]#[C:7][C:8]1([OH:19])[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1)=[O:5])[CH3:2].[H][H].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>[Pd].C(O)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][C:8]1([OH:19])[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 441036D-PsicoseHCID 59420820HCID 59420820, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59420852HCID 59420852, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To palladium on carbon (10%, 75 mg) under a nitrogen atmosphere was added a solution of tert-butyl 3-(2-(ethoxycarbonyl)ethynyl)-3-hydroxyazetidine-1-carboxylate (0.20 g, 0.74 mmol) in ethanol (10 ml). The suspension was subjected to hydrogen (Parr hydrogenation apparatus) at 45 Psi for 3 hrs. The reaction was filtered and concentrated to give an oil. The oil was purified by flash column chromatography eluting with 30 to 50% ethyl acetate/hexanes to give the title compound as a colorless oil 0.11 g, 50%. 1H NMR (CDCl3, 400 MHz) 1.28 (3H, t), 1.43 (9H, s), 2.15 (2H, t), 2.50 (2H, t), 3.32 (1H, s), 3.83 (4H, dd), 4.18 (2H, q).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customto give an oil
  4. customThe oil was purified by flash column chromatography
  5. washeluting with 30 to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b0a66f1dcb1944fb967db475d1e6ff5b
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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