Carbamate → HCID 178420766, compound

HRID 1993114Notes

Reaction equation

[NH:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[PH:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].C(=O)([O-])N.[O-]S(C(F)(F)F)(=O)=O>>[NH:1]1[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6]1.[PH:7](=[O:14])([O:11][CH2:12][C:13]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[O:8][CH2:9][C:10]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 276Carbamate

HCID 2758875Trifluoromethanesulfonate

HCID 178420765HCID 178420765, compound

Product 1

HCID 178420766HCID 178420766, compoundYield 59%

Procedure

The tetrahydropyridine-dibenzyl phosphonate 13: The compound 13 was obtained by the same procedure as described for compound 11 using the pyridine 9 (10.0 mg, 0.018 mmol) and the triflate 12 (9.4 mg, 0.022 mmol). The product 13 was purified by preparative TLC to afford the dibenzyl phosphonate 13 (8.8 mg, 59%): 1H NMR (CDCl3) δ 7.73 (d, 2H, J=8.7 Hz), 7.35 (s, 10H), 7.00 (d, 2H, J=8.7 Hz), 5.65 (d, 1H2H, J=5.1 Hz), 5.39 (br, 1H), 5.15-4.92 (m, 6H), 4.03-3.77 (m, 6H), 3.77-3.62 (m, 2H), 3.56 (br, 1H), 3.24-2.62 (m, 9H), 2.32 (d, 1H, J=13.5 Hz), 2.24-1.75 (m, 6H), 0.94 (d, 3H, J=6.6 Hz), 0.89 (d, 3H, J=6.3 Hz); 31P NMR (CDCl3) δ 25.5; MS (ESI) 842 (M+H).

Workup

customThe product 13 was purified by preparative TLC

Sources & evidence

ORD record: ord-56fb06eeec4d411f88404354f5a43599
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649015B2

Reaction notes

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