Toluene → 1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine

HRID 29058Notes

Reaction equation

HRID 29058 reaction equation
[C:1]1([CH:11]([N:13]2[CH:17]3[C:18](=O)[N:19]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:20][CH2:21][CH:16]3[CH2:15][CH2:14]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[C:1]1([CH:11]([N:13]2[CH:17]3[CH2:18][N:19]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:20][CH2:21][CH:16]3[CH2:15][CH2:14]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 670032651-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridin-7-one

Product 1

HCID 670032611-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridineYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 (4.8 g, 12 mmol) in THF (100 mL) is added slowly 1 M DIBAL in toluene, (50 mL, 50 mmol) at −78° C. The mixture is stirred at room temperature for 1 hour and quenched with 20 mL of water. The solvent is evaporated, the residue is diluted with 100 mL of 1:1 saturated Rochells salt/15% NaOH, and this extracted with EtOAc (4×50 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:9) to provide 2.3 g (48%) of the title compound. M+H+=385.26.

Workup

  1. customquenched with 20 mL of water
  2. customThe solvent is evaporated
  3. additionthe residue is diluted with 100 mL of 1:1 saturated Rochells salt/15% NaOH
  4. extractionthis extracted with EtOAc (4×50 mL)
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:9)

Sources & evidence

ORD record
ord-5948753222ef477090a7d1c6fc09bb4d
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Reaction notes

Loading…