Ammonia → HCID 58109245, compound

Participants

Reaction Steps

(R)-3-((S)-1-(4-(5-acetylthiophen-2-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxa-zinan-2-one (40 mg, 0.086 mmol) and tetraisopropoxytitanium (49 mg, 0.17 mmol) are stirred overnight in the solution of NH3 in EtOH. To this solution/paste was added NaBH4 and stirring another 24 h. The reaction was diluted with NH4OH and stirred for 1 h. The mixture was filtered through celite and rinsed with EtOAc. Water and EtOAc were added and the organic layer was separated. The aq layer is extracted with EtOAc for three times. The combined organic layer was dried over Na2SO4, filtered and concentrated to afford (6R)-3-((1S)-1-(4-(5-(1-aminoethyl)thiophen-2-yl)phenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (1.26 mg, 3%). LC-MS Method 2 tR=1.014, min, m/z=448.1; 1H NMR (CDCl3, 400 MHz): 1.33 (m, 1H), 1.47 (q, 6H), 1.90 (m, 2H), 2.13 (m, 1H), 2.22 (m, 2H), 2.82 (m, 1H), 3.50 (m, 2H), 4.33 (q, 1H), 5.58 (q, 1H), 6.81 (m, 3H), 6.98 (d, 1H), 7.25 (m, 7H).

Provenance & Evidence