Acetone → HCID 18723451, compound

HRID 842238Notes

Reaction equation

HRID 842238 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10]([C:18](CCC)=S)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.CC(C)=[O:32]>[Pd]>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:10]([CH:18]=[O:32])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 12052TriethylsilaneHCID 18723452HCID 18723452, compound

Product 1

HCID 18723451HCID 18723451, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture of 0.375 g of 10% Pd/C and 6.5 g (19.4 mmol) of 1-benzyl-3-(S)-(n-propanethiocarbonyl)-4-(S)-(ethoxycarbonyl)pyrrolidine in 30 mL acetone was added dropwise 7.5 mL (47.0 mmol) of triethylsilane over 15 min. The mixture was allowed to stir for 45 min after addition was complete. The reaction mixture was filtered through a thin pad of celite and the filtrate was concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:4) to give 4.2 g of title compound; 1H NMR (CDCl3) δ9.69 (s, 1H), 7.25-7.33 (m, 5H), 4.18 (q, 2H, J=7.1 Hz), 4.44-4.48 (m, 1H), 3.61 (d, 1H, J=13.5 Hz), 3.64 (d, 1H, J=13.5 Hz), 3.32 (m, 1H), 3.46 (m, 1H), 1.27 (t, 7.1 Hz); Mass spectrum (ESI) m/e=262 (M+1).

Workup

  1. additionafter addition
  2. filtrationThe reaction mixture was filtered through a thin pad of celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (silica, acetone:hexanes, 1:4)

Sources & evidence

ORD record
ord-a5a7314b368b4b8786a41f919f0f456f
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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