Water → HCID 69621513, compound

Participants

Reaction Steps

A catalytic amount of PdCl2(PPh3)2 (84 mg, 0.12 mmol) was added to a stirred solution of the allyl carbamate 17 (1.10 g, 2.98 mmol) and H2O (0.32 mL, 17.8 mmol) in CH2C2 (36 ml). After 5 minutes stirring at room temperature, Bu3SnH (0.89 mL, 0.96 g, 3.30 mmol) was added rapidly in one portion. A slightly exothermic reaction with vigorous gas evolution immediately ensued. The mixture was stirred for 16 hours at room temperature under nitrogen at which time TLC (50% EtOAc/Petroleum Ether) revealed the formation of amine along with the complete consumption of starting material. After diluting with CH2Cl2 (30 mL), the organic solution was dried (MgSO4), filtered and evaporated in vacuo to give an orange oil which was purified by flash chromatography (50% EtOAc/Petroleum Ether) to afford the enamine 18 as a slightly orange oil (0.57 g, 67%): 1H NMR (270 MHz, CDCl3) δ 7.53 and 7.48 (br s×2, 1H, NCH═CCH2CO2CH3), 4.35-4.13 (m, 1H, NCHCH2OTBDMS), 3.82-3.17 (m, 7H, NCH═CCH2CO2CH3, NCHCH2OTBDMS and CO2CH3), 2.64-2.04 (m, 2H, NCH═CCH2CO2CH3CH2), 0.90-0.88 (m, 9H, SiC(CH3)3), 0.09-0.00 (m, 6H, Si(CH3)2); MS (EI), m/z (relative intensity) 285, (M+., 1), 270 (M-CH3, 7), 254 (6), 242 (4), 230 (6), 228 (M-tBu, 100), 212 (4), 196 (3), 168 (13), 115 (3), 89 (10), 80 (4), 73 (13); MS (CI), m/z (relative intensity) 342 (M+.+57, 7), 302 (M+.+17, 7), 286 (M+.+1, 100), 228 (M-tBu, 100).

Provenance & Evidence