Sodium Thiosulfate → trans-4-[(Boc-amino)methyl]cyclohexanecarbaldehyde

Participants

Reaction Conditions

Reaction Steps

(4-Hydroxymethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (965 mg, 4.0 mmol) was dissolved in DCM (20 ml) and cooled down to −78° C. Dess Martin reagent (2.52 g, 6.0 mmol) was dissolved in DCM (30 ml) and added slowly to the stage 2 alcohol in solution. The reaction mixture was then stirred at r.t. for 3 h. The resulting solution was poured into a vigorously stirred saturated NaHCO3 and Na2S2O3 solution (1:1, 100 ml). The organic layer was separated and washed with brine, dried over magnesium sulfate and evaporated to dryness to yield the product (786 mg, 82% yield). 1H NMR (300 MHz, CDCl3), δ: 0.83-1.01 (2H, m, CH2), 1.15-1.24 (2H, m, CH2), 1.34 (9H, s, Boc), 1.75-1.88 (2H, m, CH2), 1.90-2.00 (2H, m, CH2), 2.05-2.18 (1H, m, CH), 2.93 (2H, t, J=6.4 Hz, CH2NH), 4.53 (1H, br. s, CHCHO), 9.55 (1H, s, CHO)

Provenance & Evidence