6-Heptenal → (3S)-1-hept-6-en-1-yl-3-methyl-L-proline

HRID 1879275Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:6][CH2:5][NH:4][C@@H:3]1[C:7]([O:9]C)=[O:8].[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17]>>[CH2:17]([N:4]1[CH2:5][CH2:6][C@H:2]([CH3:1])[C@H:3]1[C:7]([OH:9])=[O:8])[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Participants

Reactant 2

HCID 52833206-Heptenal

HCID 45089993(2s,3s)-Methyl 3-methylpyrrolidine-2-carboxylate

Product 1

HCID 68995042(3S)-1-hept-6-en-1-yl-3-methyl-L-prolineYield 80%

Procedure

Following the procedure described above for Compound 19 Steps 1-2, treatment of methyl (3S)-3-methyl-L-prolinate with hept-6-enal afforded the title compound 125 (80%) as an oil. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 5.78 (m, 1H), 5.03-4.92 (m, 2H), 3.58-3.48 (m, 2H), 3.19-3.01 (m, 2H), 3.07-2.95 (m, 1H), 2.34-2.22 (m, 1H), 2.12-2.00 (m, 3H), 1.69-1.55 (m, 3H), 1.41-1.22 (m, 4H), 1.18 (d, J 8.8, 3H).

Sources & evidence

ORD record: ord-c9397516f73044ef83593ec6b9612dbe
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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