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

HRID 391257
Notes
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Reaction equation

HRID 391257 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 82291Allylamine hydrochlorideHCID 767662601-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2,6-dibromohexanoate

Product 1

HCID 86655162(1S)-1-Methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl N-allylhexahydro-2-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes