Water → (S)-2-(tert-butoxycarbonylamino)-3-cyclopentylpropyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 1-cyclopentyl-3-hydroxypropan-2-ylcarbamate in CH2Cl2 (30 mL) Et3N (3.2 mL, 24.3 mmol) was added. The reaction mixture was cooled to 0° C. followed by dropwise addition of MsCl (1.1 g, 9.7 mmol) in CH2Cl2 (10 mL). After stirring for an additional 2 h, water (30 mL) was added and the mixture was extracted with CH2Cl2 (2×30 mL). The organic layers were washed with saturated aqueous brine, dried over MgSO4, and evaporated to give crude (S)-2-(tert-butoxycarbonylamino)-3-cyclopentylpropyl methanesulfonate that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 4.59 (brs, 1H), 4.27 (dd, J=10, 3.2 Hz, 1H), 4.17 (dd, J=10, 4 Hz, 1H), 3.86 (m, 1H), 3.02 (s, 3H), 1.81 (m, 3H), 1.60 (m, 3H), 1.50 (m, 3H), 1.46 (s, 9H), 1.09 (m, 2H).

Provenance & Evidence