Acetic Acid → Acetic acid 3-benzyl-3-aza-bicyclo[3.2.1]oct-6-yl ester
Reaction equation
[CH:1]([CH:3]1[CH2:7][CH:6]([CH:8]=O)[CH2:5][CH:4]1[O:10][C:11](=[O:13])[CH3:12])=O.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:14]([N:21]1[CH2:1][CH:3]2[CH2:7][CH:6]([CH2:5][CH:4]2[O:10][C:11](=[O:13])[CH3:12])[CH2:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
Procedure
To the above solution of acetic acid 2,4-diformyl-cyclopentyl ester was added at room temperature benzyl amine (5.8 mmol) and acetic acid (5.8 mmol) under nitrogen. After 2 h at room temperature sodium triacetoxy borohydride (25 mmol) was added and the reaction mixture was allowed to stir at room temperature for 18 h. The reaction mixture was quenched by the addition of saturated sodium bicarbonate solution (100 mL) and the phases were separated. The aqueous layer was extracted with dichloromethane (3×100 mL). The solvents were removed via rotary evaporation and the residue was purified by silica gel chromatography to afford a yellow oil (3.6 mmol). 1H NMR (CDCl3, 400 MHz): δ 7.37 (m, 2H), 7.23 (m, 3H), 5.15–4.95 (m, 1H), 3.63–3.35 (m, 2H), 2.84–2.55 (m, 2H), 2.25–2.15 (m, 4H), 2.08 (s, 3H), 1.80–1.70 (m, 2H), 1.62–1.25 (m, 2H); APCl MS m/z 260.2 (M+H)+.
Workup
- customThe reaction mixture was quenched by the addition of saturated sodium bicarbonate solution (100 mL)
- customthe phases were separated
- extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
- customThe solvents were removed via rotary evaporation
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-14730cc6f1fe4de8af1ff3c3ffb5d931
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456177B2
Reaction notes
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