Dichloromethane → HCID 86623622, compound
Reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:8]([CH3:20])=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][C:17]([O-:19])=[O:18])[CH2:11][CH2:10]2.Cl[CH2:22]Cl>>[OH:6][C:7]1[C:8]([CH3:20])=[C:9]2[C:13](=[CH:14][CH:15]=1)[C@@H:12]([CH2:16][C:17]([O:19][CH3:22])=[O:18])[CH2:11][CH2:10]2Participants
Procedure
A 1.0 M solution of boron tribromide in dichloromethane (16.2 mL, 16.2 mmol) was added to an ice-cold solution methyl (R or S)-(5-methoxy-4-methyl-indan-1-yl)acetate (1.52 g, 6.49 mmol, from Step F) in dichloromethane (5 mL). The cooling bath was removed and the reaction mixture stirred at ambient temperature. After 1 hr, the reaction mixture was slowly transferred to an ice-cold solution of methanol (50 mL). Methanol was removed in vacuo, and the residue was partitioned between EtOAc and sat. NaH2PO4. The organic layer was washed with H2O, brine, and dried over MgSO4. The mixture was filtered, concentrated in vacuo and purified by flash chromatography (5, 10% EtOAc/hexanes) on SiO2 to afford 1.22 g of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.71-1.78 (m, 1H), 2.16 (s, 3H), 2.35-2.44 (m, 2H), 2.71-2.79 (m, 2H), 2.86-2.90 (m, 1H), 3.54 (p, 1H, J=7.3 Hz), 3.72 (s, 3H), 4.83 (s, 1H), 6.61 (d, 1H, J=8.0 Hz), 6.85 (d, 1H, J=8.0 Hz).
Workup
- customThe cooling bath was removed
- customMethanol was removed in vacuo
- customthe residue was partitioned between EtOAc and sat. NaH2PO4
- washThe organic layer was washed with H2O, brine
- dry with materialdried over MgSO4
- filtrationThe mixture was filtered
- concentrationconcentrated in vacuo
- custompurified by flash chromatography (5, 10% EtOAc/hexanes) on SiO2
Sources & evidence
- ORD record
- ord-64c6c8a53f9544799611572ab49ba715
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605171B2
Reaction notes
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