(R,R)-Stilbene oxide → HCID 14391217, compound

HRID 1381532Notes

Reaction equation

HRID 1381532 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C@H:7]2[O:9][C@@H:8]2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][CH:6]=1.[CH2:16]([NH2:22])[CH:17]1[O:21][CH2:20][CH2:19][CH2:18]1>O>[C:10]1([CH:8]([OH:9])[CH:7]([NH:22][CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][O:21]2)[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 185583(R,R)-Stilbene oxideHCID 253298Tetrahydrofurfurylamine

Product 1

HCID 14391217HCID 14391217, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trans-stilbene oxide (1.96 g, 0.010 mole) and tetrahydrofurfurylamine (3.03 g, 0.030 mole) was heated at 140° C. for 2 hrs. After standing at ambient temperature for 18 hrs, the mixture was diluted with water (150 ml). An oil separated from the solution which solidified on standing for an hour. NMR and mass spectral analyses showed stilbene oxide remaining. The solid was treated with another 3.03 g of tetrahydrofurfurylamine and the mixture heated at 140° C. for another 3 hours. The reaction mixture was treated with water (150 ml) as before to obtain 2.28 g (77%) of an off-white solid after drying under ambient conditions for 18 hours. The solid was recrystallized from toluene, m.p. 167°-168° C.

Workup

  1. customAn oil separated from the solution which
  2. waiton standing for an hour
  3. additionThe solid was treated with another 3.03 g of tetrahydrofurfurylamine
  4. temperaturethe mixture heated at 140° C. for another 3 hours
  5. additionThe reaction mixture was treated with water (150 ml) as before

Sources & evidence

ORD record
ord-94cea6318c7a4433b3b6f0c393d9774c
Source dataset
uspto-grants-1989_02
Patent number
US04803200

Reaction notes

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