Sodium Iodide → (1S)-1-Methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl N-allylhexahydro-2-pyridinecarboxylate

HRID 391257Notes

Reaction equation

Br[CH:2]([CH2:15][CH2:16][CH2:17][CH2:18]Br)[C:3]([O:5][CH:6]([CH3:14])[C:7](=[O:13])[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:4].[Na+].[I-].C(N(CC)CC)C.Cl.[CH2:30]([NH2:33])[CH:31]=[CH2:32]>O1CCCC1>[CH2:30]([N:33]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:2]1[C:3]([O:5][C@@H:6]([CH3:14])[C:7](=[O:13])[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:4])[CH:31]=[CH2:32]

Participants

Conditions

Temperature: 20 °C

Procedure

TO 1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2,6-dibromohexanoate (295 mg, 0.75 mmol), NaI (225 mg, 1.5 mmol), triethylamine (303 mg, 3.0 mmol) and tetrahydrofuran (4 mL) were added. Subsequently, allylamine hydrochloride (84.2 mg, 0.9 mmol) and tetrahydrofuran (4 mL) were added thereto. The mixture was stirred at 20° C. for 4 hours and then at 40° C. for 15 hours. It was confirmed with NMR analysis of the reaction solution that the conversion ratio was 100% and the diastereo ratio was 75:25.

Workup

waitat 40° C. for 15 hours

Sources & evidence

ORD record: ord-ef646b110d554b858846bec6ad6d70a6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383833B2

Reaction notes

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