反応 #76054

反応方程式

triethylamine

4-[(2R)-2-amino-3-hydroxypropyl]phenol

tert-butyl isothiocyanate

→

N-(tert-butyl)-N′-[(1R)-1-hydroxymethyl-2-(4-hydroxyphenyl)ethyl]thiourea

溶媒

ethanol

反応条件

後処理

1. 1
   温度is then heated at a temperature in the region of 60° C. for 4 hours
2. 2
   温度After cooling
3. 3
   その他the reaction medium is evaporated under reduced pressure (1 kPa) at a temperature in the region of 40° C.
4. 4
   その他chromatographed under an argon pressure of 60 kPa on a column of silica gel (particle size 40-63μ; diameter 2.5 cm; height 29 cm)
5. 5
   洗浄eluting with a mixture of dichloromethane/methanol (98/2 by volume)
6. 6
   workup.ADDITIONThe fractions containing the expected product
7. 7
   濃縮concentrated under the above conditions

実験手順

0.15 cm3 of triethylamine is added to a solution of 0.2 g of 4-[(2R)-2-amino-3-hydroxypropyl]phenol in 10 cm3 of absolute ethanol, followed by addition of 0.18 cm3 of tert-butyl isothiocyanate. The mixture is stirred at a temperature in the region of 20° C. for 18 hours and is then heated at a temperature in the region of 60° C. for 4 hours. After cooling, the reaction medium is evaporated under reduced pressure (1 kPa) at a temperature in the region of 40° C. and then chromatographed under an argon pressure of 60 kPa on a column of silica gel (particle size 40-63μ; diameter 2.5 cm; height 29 cm), eluting with a mixture of dichloromethane/methanol (98/2 by volume). The fractions containing the expected product are combined and then concentrated under the above conditions. 0.2 g of N-(tert-butyl)-N′-[(1R)-1-hydroxymethyl-2-(4-hydroxyphenyl)ethyl]thiourea is obtained in the form of a colorless viscous oil [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 1.42 (s: 9H); 2.63 (dd, J=13.5 and 8 Hz: 1H); 2.72 (dd, J=13.5 and 5.5 Hz: 1H); from 3.25 to 3.40 (mt: 2H); 4.29 (unresolved complex: 1H); 4.83 (t, J=4.5 Hz: 1H); 6.67 (d, J=8 Hz: 2H); 7.05 (d, J=8 Hz: 2H); 7.15 (d, J=8 Hz: 1H); 7.26 (broad s: 1H); 9.16 (s: 1H)].

出典