Iodoethane → 6-benzyl-1-ethyloctahydro-1H-pyrrolo[3,4-b]pyridine

HRID 712489Notes

Reaction equation

HRID 712489 reaction equation
[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([NH:11][CH2:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:20][CH3:21]>C1COCC1>[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([N:11]([CH2:20][CH3:21])[CH2:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 113563766-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine

Product 1

HCID 867294996-benzyl-1-ethyloctahydro-1H-pyrrolo[3,4-b]pyridineYield 45.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine (5.00 g) in THF was added 80% NaH (3.00 g) at room temperature. The reaction mixture was stirred for 30 min, and 5.3 mL of iodoethane was added dropwise. The reaction mixture was stirred for another 5 h, and then quenched with ice-water. The resulted mixture was extracted with CH2Cl2 (70 mL×5). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH) to give the title compound as a pale yellow solid (2.58 g, 45.60%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 245.2 (M+1).

Workup

  1. stirringThe reaction mixture was stirred for another 5 h
  2. customquenched with ice-water
  3. extractionThe resulted mixture was extracted with CH2Cl2 (70 mL×5)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed with a silica gel column (eluting agent: 30:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-892c5dcd9c524bddb90de900dac7e0ce
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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