Dichloromethane → HCID 11522057, compound

Participants

Reaction Steps

N-Boc-2-(4-methoxybenzyl)morpholine was prepared using the same procedure as described for example 9, intermediate (a), but starting with racemic epichlorohydrin. N-Boc-2-(4-methoxybenzyl) (0.16 mmol) was dissolved in dichloromethane (1.5 mmol) and N-bromosuccinimide (28 mg, 0.16 mmol) added. The reaction was shaken for 18 hrs at room temperature and then further N-bromosuccinimide (11 mg, 0.06 mmol) added. The reaction was shaken for a further 2 hrs, Na2S2O3 (10% w/v aqueous solution, 1 mL) added and the mixture shaken for 40 minutes. The mixture was poured on to an HMN column (25 g) and washed with dichloromethane (10 mL) and the liquors concentrated in vacuo. The residue was dissolved in dichloromethane (1.5 mL), treated with TFA (1 mL) and shaken for 90 minutes at room temperature. The reaction mixture was added directly to an SCX-2 column (5 g) and washed with dichloromethane (2 mL×2) and methanol (2 mL). The SCX-2 column was then washed with ammonia (2N in methanol, 3×2 mL and 2×2.5 mL). Combined ammonia washes were concentrated in vacuo. The residue was dissolved in IPA (2 mL) and diethyl ether (2 mL) and treated with MP-carbonate (3.1 mmol/g, 300 mg) and shaken for 30 minutes. The suspensions were filtered and the concentrated in vacuo to yield the desired 2-(3-Bromo-4-methoxy-benzyl)-morpholine example 72, as a beige gum (18 mg).

Provenance & Evidence