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Methyl iodide → HCID 86646601, compound

HRID 1963238
Notes
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Reaction equation

HRID 1963238 reaction equation
[NH:1]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[N:4][N:3]=[N:2]1.IC.[C:29]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:29][N:3]1[N:2]=[N:1][C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:4]1.[CH3:29][N:4]1[C:5]([CH:6]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][CH2:8][N:7]2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:1][N:2]=[N:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178469255HCID 178469255, compound

Product 2

HCID 66734713HCID 66734713, compoundYield 32%HCID 86646601HCID 86646601, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

1-Benzyl 4-ethyl 2-(1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (3.45 g, 9.60 mmol) was dissolved in acetone (20 mL) and iodomethane (2.99 mL, 48.00 mmol) and K2CO3 (3.98 g, 28.80 mmol) were added. The mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted twice with EtOAc and the combined organic phase was washed with water and evaporated. The crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV). 1-Benzyl 4-ethyl 2-(2-methyl-2H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.84 g, 51%) and 1-benzyl 4-ethyl 2-(1-methyl-1H-tetrazol-5-yl)piperidine-1,4-dicarboxylate (1.14 g, 32%) were isolated. 2-Methyl-isomer: 1H NMR (400 MHz, cdcl3) δ 1.15 (t, 3H), 1.75-1.87 (m, 1H), 2.02-2.11 (m, 1H), 2.27-2.37 (m, 1H), 2.66-2.78 (m, 2H), 3.55-3.65 (m, 1H), 3.75-3.86 (m, 1H), 3.90-3.99 (m, 1H), 4.01-4.09 (m, 1H), 4.25 (s, 3H), 5.13 (q, 2H), 5.55-5.62 (m, 1H), 7.25-7.38 (m, 5H). MS m/z 374 (M+H)+. 3-Methyl-isomer: MS m/z 374 (M+H)+

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. washthe combined organic phase was washed with water
  4. customevaporated
  5. customThe crude product was purified on a 100 g Biotage column with heptane/EtOAc 88/12-0/100 over 12 column volumes (CV)

Sources & evidence

ORD record
ord-693130be051b4bf4bbf326f17a010ea6
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415378B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes