反应详情

To a solution of 3 (1.68 g, 8.08 mmol) and cyclopropylmethyl bromide (1.31 g, 9.70 mmol) in toluene (25 mL) at 0° C. was added a solution of KHMDS (0.5 M in toluene, 17.8 mL, 8.89 mmol) and stirred for 18 h. The reaction was partially concentrated under vacuum and purified by column chromatography (silica gel) using 0 to 65% EtOAc in hexanes to 4a (minor diastereomer, 290 mg, 14%) and 4b (major diastereomer, 685 mg, 32%) as clear oils; 1H-nmr (400 MHz, CDCl3) δ (minor diastereomer) 3.60 (td, J=12.0, 4.0 Hz, 1H), 3.49 (d, J=12.0 Hz, 1H), 3.41 (d, J=12.0 Hz, 1H), 2.28-2.24 (m, 1H), 1.43 (s, 9H), 1.43-1.28 (m, 2H), 0.94-0.86 (m, 1H), 0.66-0.59 (m, 1H), 0.21 (q, J=6.0 Hz, 1H); LC-MS (214 nM) 3.18 min (>98%), m/z 207.1 [M-tBu]. 1H-nmr (400 MHz, CDCl3) δ (major diastereomer) 3.81 (d, J=12.0 Hz, 1H), 3.75 (d, J=12.0 Hz, 1H), 3.57 (td, J=12.0, 4.0 Hz, 1H), 1.83-1.78 (m, 2H), 1.43 (s, 9H), 1.46-1.40 (m, 2H), 0.92-0.84 (m, 1H), 0.61-0.52 (m, 2H), 0.22-0.16 (m, 2H); LC-MS (214 nM) 3.11 min (>98%), m/z 162.9 [M-Boc], 285.2 [M+Na].

1. concentrationThe reaction was partially concentrated under vacuum
2. custompurified by column chromatography (silica gel)
3. customLC-MS (214 nM) 3.18 min (>98%), m/z 207.1 [M-tBu]
4. customLC-MS (214 nM) 3.11 min (>98%), m/z 162.9 [M-Boc], 285.2 [M+Na]