2-amino-2-methyl-1-propanol (Aldrich)
1,2-diisothiocyanato-cyclohexane (Previously prepared, see CSSP604) 
THF (distilled over potassium)

2-amino-2-methyl-1-propanol (0.795 g, 8.92 mmol) was placed in a Schlenk vessel and purged with argon. THF (20 mL) was added and the Schlenk vessel degassed. The 1,2-diisothiocyanato-cyclohexane 2 (0.800 g, 4.04 mmol) was dissolved THF and then added to the solution. The solution was then heated to reflux (75 °C) for 72 h under static vacuum. The THF was then evaporated under reduced pressure to leave a sticky white solid. The compound was washed with warm hexane, cooled and the solid filtered off. The isolated solid was then was used without further purification. For purposes of obtaining a sample for analysis the following work up procedure was performed: Hexane (100 mL) was added and the mixture heated with stirring to remove the excess amino alcohol. The solid was then isolated by filtration and residual solvent removed by evaporation under reduced pressure. The white solid was redissolved in chloroform and the solution left in a freezer overnight to afford crystallisation. The white solid was then filtered off and any residual ether removed under reduced pressure (yield 53 %, 0.800 g).

¹H NMR (293 K, d₁-chloroform) d 1.14 (s, 6H, CH₃), 1.28 (m, 4H, cyclohexyl-CH₂), 1.31 (s, 6H, CH₃), 1.70 (m, 2H, cyclohexyl-CH₂), 1.99 (m, 2H, cyclohexyl-CH₂), 3.39 (d, ³J_HH = 12 Hz, 2H, CH₂,), 3.69 (d, 2H, cyclohexyl-CH₂), 4.16 (m, 2H, cyclohexyl-CH), 5.86 (s, 2H, NH), 9.34 (s, 2H, NH).

¹³C{¹H} NMR (293 K d₁-chloroform) d 21.1 (CH₃), 24.7 (cyclohexyl-CH₂), 27.3 (CH₃), 32.7 (cyclohexyl-CH₂), 57.9 (NCq(CH₃)₂), 59.8 (cyclohexyl-CH), 69.7 (CH₂), 178.4 (NCqN).

IR (DCM layer, cm^-1): 3240, 3072, 2930, 2857, 1594, 1527, 1462, 1411, 1369, 1259, 1230, 1051, 915, 731, 631.

Anal. Calcd. for C₁₆H₃₂N₄S₂O₂: C, 51.03; H, 8.56; N, 14.88.  Found: C, 50.87 ; H, 8.52; N, 14.78.

MS (EI) m/z 376 (M⁺).