Hydrochloric Acid → (S)-2-amino-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethylpentan-1-one hydrochloride

Participants

Reaction Steps

A solution of HCl in 1,4-dioxane (4.0M, 25 mL, 100 mmol) was added to tert-butyl (S)-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethyl-1-oxopentan-2-ylcarbamate (1.73 g, 4.48 mmol). The solution was stirred for 2 hours then the solvents were removed in vacuo and the residue azeotroped with toluene (1×50 mL then 1×25 mL) to leave (S)-2-amino-1-((3R,3aR,6R,6aS)-3-hydroxy-6-methoxydihydro-2H-furo[3,2-b]pyrrol-4(5H,6H,6aH)-yl)-4,4-dimethylpentan-1-one hydrochloride as an off-white solid which was used without further purification. TLC (Rf=0.0, EtOAc:heptane 2:1), analytical HPLC main peak, Rt=4.047 min., HPLC-MS 287.2 [M+H]+, 595.3 [2M+Na]+; δC (125 MHz, CD3OH) 29.66 (C(CH3)3), 30.45 (C(CH3)3), 44.51/49.24 (NCH2CHOCH3 and CH2C(CH3)3), 50.03 (CHCH2C(CH3)3), 57.85 (OCH3), 70.64 (CHCHOH), 74.83 (CHCHOH), 75.56 (CH2CHOH), 78.13 and 79.11 (CHCHOCH3), 169.80/169.98 (NC═O).

Provenance & Evidence