N-ACETYL-(2S)-BORNANE 10,2-SULTAM

Preparation of XVIII [0222] To a solution of compound XVI (21.45 g, 83.33 mmol) in dry DCM (215 mL) was added Bu2BOTf (100 mL, 1 M) at 0 C. under an atmosphere of N2, the reaction mixture was stirred for 30 minutes, then DIPEA (17.3 mL, 104.16 mmol) was added, and the reacting mixture was stirred for another 30 minutes. After the resulting mixture was cooled to -78 C., XVII (14.95 g, 116.67 mmol) was added dropwise. The reaction temperature was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with sat. aq. NH4Cl, then extracted with EtOAc. The combined organic layer were dried over Na2SO4, filtered and evaporated. The residue was purified by column, eluting with petroleum ether/EtOAc=20:1 to 5:1) to give XVIII (23 g, yield: 71.9%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 4.30 (m, 1H), 3.87 (m, 1H), 3.45 (m, 2H), 3.25 (m, 1H), 2.80 (m, 2H), 2.55 (m, 2H), 2.08 (m, 2H), 1.89 (m, 3H), 1.37 (m, 2H), 1.17 (s, 3H), 1.15 (s, 3H), 1.12 (s, 3H), 1.02 (t, J=7.2 Hz, 3H), 0.97 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 216.1, 171.5, 73.0, 65.4, 53.1, 51.2, 48.7, 48.0, 44.9, 38.6, 38.0, 33.1, 31.4, 26.6, 21.8, 21.06, 20.1, 19.4, 8.1.

Molecular Weight:257.35
XLogP3:1.5
Hydrogen Bond Acceptor Count:3
Exact Mass:257.10856464
Monoisotopic Mass:257.10856464
Topological Polar Surface Area:62.8
Heavy Atom Count:17
Complexity:490
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes