Water → HCID 53665728, compound

HRID 365312Notes

Reaction equation

HRID 365312 reaction equation
[O:1]1[CH:9]2[CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]2.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.O>C(Cl)Cl>[CH2:10]([NH:17][C@@H:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][C@H:9]1[OH:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 96238HCID 96238, compoundHCID 2733225Ytterbium triflate

Product 1

HCID 53665728HCID 53665728, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5,6-epoxycyclooctene III (10.0 g, 0.081 mol) in dry CH2Cl2 (100 ml) kept under nitrogen atmosphere, benzylamine (10.35 g, 0.097 mol) and Ytterbium(III) trifluoromethanesulfonate (4.96 g, 0.008 mol) were added and the mixture was stirred for 24 hrs at room temperature. Extractive work-up of the reaction mixture with water and CH2Cl2 gave the title product as a white solid (yield 83%). m.p.: 70-71° C., b.p:140° C./1 mm Hg. 1H NMR (CDCl3): δ 7.59-7.56 (m, 2H, ArH), 7.38-7.35 (m, 3H, ArH), 5.64-5.44 (m, 2H, CH=CH), 5.42-5.00 (bs, D2O exchangeable, OH) 4.07 (AB syst, 2H, J=12.57 Hz, PhCH2), 3.75-3.65 (m, 1H, CHOH), 3.00-3.15 (m, 1H, CHNH--), 2.35-2.02 (m, 6H), 1.95-1.42 (m, 2H).

Sources & evidence

ORD record
ord-b4553e7c3c3046d7ae2379c0296ba110
Source dataset
uspto-grants-2000_10
Patent number
US06127362

Reaction notes

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