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

HRID 391256
Notes
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Reaction equation

HRID 391256 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.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH2:29]([N:36]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])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7504BenzylamineHCID 8471TriethylamineHCID 767662601-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2,6-dibromohexanoate

Product 1

HCID 86655161(1S)-1-Methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl N-benzylhexahydro-2-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
40 °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) and tetrahydrofuran (4 mL) were added. The mixture was stirred at 40° C. for 1.5 hours. Next, triethylamine (84 mg, 0.83 mmol), benzylamine (97 mg, 0.90 mmol) and tetrahydrofuran (4 mL) were added thereto. The mixture was stirred at 20° C. for 15 hours. It was confirmed with NMR analysis of the reaction solution that the conversion ration was 83% and the diastereo ratio calculated from the NMR analysis was 79:21.

Workup

  1. stirringThe mixture was stirred at 20° C. for 15 hours

Sources & evidence

ORD record
ord-4743b6965be849d3954ad5182bde5d5f
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