Sodium Hydroxide → cyclopropyl(1,3-thiazol-2-yl)methanamine

Reaction equation

[CH:1]1([C:4]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)=O)[CH2:3][CH2:2]1.[BH3-]C#[N:13].[Na+].[OH-].[Na+]>CO>[CH:1]1([CH:4]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)[NH2:13])[CH2:3][CH2:2]1

Participants

Procedure

The title compound was synthesized according to General Method F, utilizing cyclopropyl(thiazol-2-yl)methanone (0.28 g, 1.8 mmol), NH4OAc (1.7 g, 22 mmol), NaCNBH3 (0.46 g, 7.3 mmol), and MeOH (30 mL). Aq. NaOH (2 M, 15 mL) was added and the product was extracted into EtOAc (3×40 mL). The combined EtOAc layer was dried (MgSO4), filtered, concentrated to dryness. Purification by flash chromatography (Biotage Isolera, 25 g HP-SIL, 60-100% EtOAc in hexanes) gave the title compound as a yellow oil (0.15 g, 55% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.63 (d, J=2.8 Hz, 1H), 7.18 (d, J=2.8 Hz, 1H), 3.50 (d, J=8.5 Hz, 1H), 2.35 (br. s., 2H), 1.03-1.16 (m, 1H), 0.48-0.63 (m, 2H), 0.26-0.47 (m, 2H); MS ESI 138.0 [M-NH2]+, calcd for [C7H10N2S—NH2]+138.0.