Lawesson's reagent → HCID 90442641, compound

HRID 513216Notes

Reaction equation

HRID 513216 reaction equation
O=[C:2]1[NH:9][CH2:8][CH:7]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[CH2:4][CH2:5][CH2:6]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1COCC1>[S:27]=[C:2]1[NH:9][CH2:8][CH:7]2[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[CH2:4][CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22640051HCID 22640051, compound

Product 1

HCID 90442641HCID 90442641, compoundYield 144.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate (733 mg, 3.05 mmol) in THF (10 mL) was added Lawesson's reagent (700 mg, 1.68 mmol). The mixture was stirred at room temperature overnight and then concentrated in vacuo. The residue was dissolved in EtOAc and washed 3× with saturated aqueous NaHCO3 solution. The combined aqueous layers were extracted several times with EtOAc and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on SiO2 eluting with EtOAc/Hex to afford the title compound as a colorless foam (622 mg, 79%). MS (ESI): mass calcd. C12H20N2O2S, 256.12; m/z found, 257.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.54-8.20 (m, 1H), 5.23-4.97 (m, 1H), 4.66-4.33 (m, 1H), 3.81-3.63 (m, 1H), 3.28-3.17 (m, 1H), 2.22-2.11 (m, 1H), 1.90-1.58 (m, 5H), 1.47 (s, 9H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed 3× with saturated aqueous NaHCO3 solution
  4. extractionThe combined aqueous layers were extracted several times with EtOAc
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on SiO2 eluting with EtOAc/Hex

Sources & evidence

ORD record
ord-f64c0be478864036a19bf7ec907d2f4f
Source dataset
uspto-grants-2015_08
Patent number
US09102686B2

Reaction notes

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