반응 #67651

반응 방정식

sodium triacetoxyborohydride

acetic acid

product

N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]amine

acetaldehyde

→

title compound

수율 47.5%

N-[(2S)-2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-[2-(tert-butoxycarbonylamino)-3-(phenylmethoxy)propyl]-N-ethylamine

수율 47.5%

용매

CH2Cl2

dichloroethane

반응 조건

후처리

1. 1
   workup.STIRRINGAfter stirring at ambient temperature overnight
2. 2
   세척washed with saturated aqueous NaHCO3 (2×20 mL) and brine
3. 3
   건조dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by column chromatography on silica gel (hexanes:ethyl acetate, 1:1)

실험 절차

The product from Example 17C (0.15 g) in dichloroethane (5 mL) was treated with acetaldehyde (20 μL, 0.36 mmol). After stirring at ambient temperature for 10 minutes, the mixture was treated with sodium triacetoxyborohydride (0.10 g, 0.47 mmol) and acetic acid (20 μL, 0.35 mmol). After stirring at ambient temperature overnight, the mixture was diluted with CH2Cl2 (20 mL), washed with saturated aqueous NaHCO3 (2×20 mL) and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexanes:ethyl acetate, 1:1) to provide the title compound (75 mg, 44%). 1H NMR (CDCl3) δ 7.36-7.24 (m, 10H), 4.93 (br s, 2H), 4.54-4.41 (m, 4H), 3.77-3.63 (m, 2H), 3.61 (dd, J=3.4, 9.2 Hz, 2H), 3.5-3.38 (m, 2H), 2.66-2.42 (m, 6H), 1.44 (s, 9H), 1.43 (s, 9H), 0.98 (t, J=7.1 Hz, 1.5H), 0.96 (t, J=7.1 Hz, 1.5H); MS (APCl+) m/z 572 (M+H)+.

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