T-BOC


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AcronymDefinition
T-BOCTert-Butyloxycarbonyl
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(R)-tert-Butyl-3-tosylpyrrolidine-1-carboxylate(2, Method E) was isolated asa water-white oilusing pyridine as the base (16%); [sup.1]HNMR [delta] 7.67 (d, 2H, ArH); 7.38 (d, 2H, ArH); 4.92 (m, [sup.1]H, ring 3-CH); 3.32-3.42 (m, 4H, ring 2- and 5-C[H.sub.2]); 2.32 (s, 3H, ArC[H.sub.3]); 1.96-2.15 (m, 2H, ring 4-C[H.sub.2]), 1.32 (s, 9H, t-BOC C[H.sub.3]); EIMS (70 eV): 282 [[M-t-Bu].sup.+], 268 [[M-t-BuO].sup.+]; 155 [[[C.sub.7][H.sub.7]S[O.sub.2]].sup.+]; 113 [[[C.sub.5][H.sub.7]N[O.sub.2]].sup.+], 91 [[[C.sub.7][H.sub.7]].sup.+]; 57 [[t-Bu].sup.+].
(R, E)-tert-Butyl-3-[(2-methylbut-2-enoyl)oxy]pyrrolidine -1-carboxylate (3, Method A) was isolated as a pale yellow oil (85.4%); [sup.1]H NMR [delta] 6.73 (q, [sup.1]H, vinylic CH); 4.11 (p, [sup.1]H, 3-O-CH); 3.43 (m, 2H, ring N-C[H.sub.2]); 3.31 (m, 2H, ring N-C[H.sub.2]); 1.93 (br m, 2H, diastereotopic ring 4-C[H.sub.2]); 1.78 (d, 3H, vinylic C[H.sub.3]); 1.68 (s, 3H, vinylic C[H.sub.3]); 1.33 (s, 9H; t-BOC C[H.sub.3]); [sup.13]C NMR [delta] 14.1, 14.3, 14.4, 14.6, 28.5, 30.9, 31.7, 43.6, 44.2, 72.7, 74.1, 79.6, 133.3, 133.5, 137.9, 138.1, 152.5, 154.6, 167.5, and 179.9; IR (film) 3155, 2984, 1692, 1469, 1382, 1261, 1165, and 1095 [cm.sup.?1]; EIMS (70eV): 196 [[M-t-BuO].sup.+], 113 [[[C.sub.5][H.sub.7]N[O.sub.2]].sup.+], and 83 [[OC[C.sub.4][H.sub.7]].sup.+]; 57 [[t-Bu].sup.+].
(S)-tert-Butyl-3-(acryloyloxy)pyrrolidine-1-carboxylate (12, Method A) was isolated as a pale yellow oil (43.6%); [sup.1]H NMR [delta] 6.30 (d, [delta] = 5.8Hz, [sup.1]H, vinylic CH); 5.99 (dd, [delta] = 3.5, 5.8Hz, [sup.1]H, vinylic CH); 5.73 (d, [delta] = 3.5 Hz, [sup.1]H, vinylic CH); 5.23 (br m, [sup.1]H, ring diastereotopic 4-CH); 3.47 (m, 2H, N-C[H.sub.2]); 3.33 (m, 2H, N-C[H.sub.2]); 1.95 (m, 2H, ring 4-C[H.sub.2]); 1.34 (s, 9H, t-BOC C[H.sub.3]); [sup.13]C NMR [delta] 28.6, 30.9, 31.7, 43.7, 44.12, 51.5, 51.9, 73.3, 74.1, 79.7, 128.4, 131.4, 154.5, and 165.8; IR (film) 3061, 2979, 2885, 1727, 1620, 1479, 1412, 1366, 1297, 1270, 1192, 1117, and 1096 [cm.sup.?1]; EIMS (70 eV): 168 [[M-t-BuO].sup.+], 113 [[[C.sub.5][H.sub.7]N[O.sub.2]].sup.+], and 57 [[t-Bu].sup.+].