Sodium Hydroxide → 8-Benzyl-8-azabicyclo(3.2.1)octan-3-one

HRID 1860512Notes

Reaction equation

CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.Cl.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O=[C:20]([CH2:25]C(O)=O)[CH2:21]C(O)=O.C([O-])(=O)C.[Na+].[OH-].[Na+]>Cl>[CH2:11]([N:18]1[CH:6]2[CH2:5][CH2:25][CH:20]1[CH2:21][C:3](=[O:4])[CH2:7]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,5-dimethoxytetrahydrofuran (17.1 g, 132.2 mmol) was dissolved in 0.025 M HCl (56 mL) and the mixture was stirred at 0° C. for 16 h. Benzylamine hydrochloride (22.8 g, 158.6 mmol) and 3-oxopentanedioic acid (19.3 g, 132.2 mmol) followed by aqueous sodium acetate (105 mL, 0.69 M). The reaction mixture was warmed to room temperature and stirred for lh then heated to 50° C. for 1.5 h. After cooling back to rt the mixture was basified with sodium hydroxide and extracted with EtOAc (3×) The combined organic portions were dried over sodium sulfate and concentrated. Flash chromatography (450 g silica, 50/1 CH2Cl2/MeOH), gave the desired product. 1H NMR (500 MHz, CDCl3) δ1.65 (m, 2H), 2.05-2.15 (m, 2H), 2.2 (s, 1H), 2.23 (s, 1H), 2.69 (m, 1H), 2.72 (m, 1H), 3.48 (s, 2H), 7.2-7.3 (m, 1H), 7.33-7.4 (m, 4H).

Workup

temperatureThe reaction mixture was warmed to room temperature
stirringstirred for lh
temperaturethen heated to 50° C. for 1.5 h
temperatureAfter cooling back to rt the mixture
extractionextracted with EtOAc (3×) The combined organic portions
dry with materialwere dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-a065a2251b5a4bf1a2d3e7be5f77dcdc
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531484B2

Reaction notes

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