Ethyl Acetate → HCID 86638633, compound

HRID 1669612Notes

Reaction equation

HRID 1669612 reaction equation
[N:1]([C@@H:4]([C@H:7]1[CH2:11][CH2:10][CH2:9][O:8]1)[CH2:5][CH3:6])=[N+]=[N-].C1(P([C:25]2[CH:30]=[CH:29]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31](=[O:34])(O)[O-:32].[Na+].[CH3:36]COC(C)=O>C1COCC1>[O:8]1[CH2:9][CH2:10][CH2:11][C@@H:7]1[C@H:4]([NH:1][C:31](=[O:34])[O:32][C:30]([CH3:29])([CH3:25])[CH3:36])[CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 86638634HCID 86638634, compound

Product 1

HCID 86638633HCID 86638633, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-2-((R)-1-azidopropyl)tetrahydrofuran (step 1) (2.11 g, 13.6 mmol) in THF (60 ml) and H20 (10 ml) was added triphenylphosphine (4.28 g, 16.32 mmol). The reaction was heated at 50° C. overnight and then allowed to cool to RT. Sodium bicarbonate (11.42 g, 136 mmol) and Boc-anhydride (4.16 g, 19.04 mmol) were added and the reaction mixture was heated at 40° C. The reaction was allowed to cool to RT and EtOAc was added. The aqueous and organic layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product mixture was purified by flash chromatography on silica gel (40 g) eluting with an EtOAc/iso-hexane (gradient 0-40%) to afford the title product; 1H NMR (CDCl3) δ 0.98 (3H, t, CH3), 1.45 (9H, s, (CH3)3), 1.6 (3H, m), 1.9 (3H, m), 3.5 (1H, m), 3.7 (1H, m), 3.85 (2H, m), 4.6 (1H, m).

Workup

  1. temperatureto cool to RT
  2. temperaturethe reaction mixture was heated at 40° C
  3. temperatureto cool to RT
  4. customThe aqueous and organic layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product mixture was purified by flash chromatography on silica gel (40 g)
  10. washeluting with an EtOAc/iso-hexane (gradient 0-40%)

Sources & evidence

ORD record
ord-f74a9c88af404da592baa8c8e3760761
Source dataset
uspto-grants-2011_08
Patent number
US07989497B2

Reaction notes

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