Benzylamine → HCID 66844756, compound

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Reaction Steps

Benzylamine (2.76 mmol, 2.3 eq) is added to a solution of (1S,3S,5S)-3-formyl-2-azabicyclo[3.3.0]octane-2-carboxylic acid tert-butyl ester (1.2 mmol, 1.0 eq) in chloroform (10 mL). The mixture is stirred for 5 min, treated with sodium triacetoxyborohydride (4.8 mmol, 4.0 eq) and acetic acid (0.05 mL), stirred for additional 14 h and poured into sat. NaHCO3 solution. DCM is added, the layers are separated and the aqueous layer is extracted with DCM. The combined organic layers are washed with water (100 mL) and concentrated in vacuo. The residue is dissolved in ether and extracted three times with hydrochloric acid (0.1 M). The combined aqueous layers are extracted once with ether, made basic (pH 9-10) by addition of NaOH solution (1.0M) and extracted three times with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give the desired benzylamine which is used without further purification. LC-MS: tR=0.89 min; [M+H]+=331.5.

Provenance & Evidence