(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine → HCID 21034348, compound

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Reaction Steps

The protected carbinolamine 149 (0.8 g, 1.3 mmol) was added to a 5% solution of piperidine in CH3CN (12 mL, 5 eq. of piperidine). The mixture was allowed to stir for 12 hours, extracted with water (2×50 mL) and the organic phase was evaporated under reduced pressure to yield a pale yellow oil (0.24 g, 50%): 1H NMR (270 MHz, CDCl3) δ1.9-2.2 (m, 4H); 3.45-3.7 (m, 3H); 4.26 (d, J=12.1 Hz, 1H); 4.55 (m, 3H); 5.18 (d, J=12.1 Hz, 1H); 5.61 (d, J=10.3 Hz, 1H); 6.61 (s, 1H); 6.69 (d, J=7.3 Hz, 1H); 7.56 (d, J=8.2 Hz, 1H). 13C NMR (67.8 MHz, CDCl3) δ23.0; 28.7; 46.3; 59.8; 74.9; 95.1; 114.8; 116.5; 130.4; 135.3; 154.4; 167.3. IR (Nujol): cm−1 3340, 3224, 3000-2800, 1714, 1602, 1460, 1311, 1208, 1141, 1061, 826, 759, 665. MS: m/e (relative intensity) 407 (M+. , 40), 381 (5), 340 (10), 309 (25), 161 (100), 134 (15), 105 (15), 70 (80). HRMS Calculated for C15H16C13N3O4. 407.0206. Found: 407.0206. [α]25D=+47.8° (c=0.5, CHCl3).

Provenance & Evidence