4-Methylmorpholine → HCID 178453954, compound

Participants

Reaction Conditions

Reaction Steps

cis-4-[(tert-Butoxy)carbonylamino]cyclohexane carboxylic acid (2.6 g, 10.68 mmol) was dissolved in THF (20 mL) and cooled to −10° C. (MeOH-ice). N-Methyl morpholine was added followed by isobutyl chloroformate (1.175 mL, 10.68 mmol). After 10 min, NaBH4 was added as a solid in one portion (1.213 g, 32.06 mmol). The reaction mixture was warmed to 0° C. and methanol was added dropwise (13.35 mL). After 30 min, the reaction was quenched with 5% aqueous KHSO4. The reaction was monitored by LC-MS until complete. The crude product was extracted with ethyl acetate and the combined extracts were dried over Na2SO4. A colorless oil was obtained and solidified slowly at room temperature. The product and purity were assessed by LC-MS and 1H NMR. No further purification was necessary. (quantitative yield) ES-MS (m/z) 230.

Provenance & Evidence