Naphthalene → HCID 70007021, compound
Reaction equation
[Li].C1C2C(=CC=CC=2)C=CC=1.[NH2:12][C@@H:13]1[CH2:19][CH2:18][C@@H:17]2[N:20]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@:14]1([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:15][C@H:16]2S(C1C=CC=CC=1)(=O)=O>O1CCCC1>[NH2:12][C@@H:13]1[CH2:19][CH2:18][C@@H:17]2[N:20]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@@:14]1([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:15][CH2:16]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Lithium (175 mg, 25 mmol) was added to a solution of naphthalene (3.2 g, 25 mmol) in tetrahydrofuran (25 mL), and the mixture sonicated for 2 hours. The green solution formed was then slowly added to a solution of (1R*,2R*,5S*,6R*)-2-amino-8-benzyl-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane (Description 8; 2.0 g, 4.6 mmol) in tetrahydrofuran (50 mL), already cooled to −78° C. The mixture was stirred at −78° C. for 1 hour, then quenched with aqueous saturated ammonium chloride solution (50mL). After warming to ambient temperature, the mixture was extracted with ethyl acetate (2×100 mL) and the extracts dried (MgSO4). Concentration in vacuo yielded a solid, which was purified by silica chromatography to give the title compound as a gum (900 mg, 3.1 mmol).
Workup
- customthe mixture sonicated for 2 hours
- customThe green solution formed
- customquenched with aqueous saturated ammonium chloride solution (50mL)
- temperatureAfter warming to ambient temperature
- extractionthe mixture was extracted with ethyl acetate (2×100 mL)
- dry with materialthe extracts dried (MgSO4)
- concentrationConcentration in vacuo
- customyielded a solid, which
- customwas purified by silica chromatography
Sources & evidence
- ORD record
- ord-6879522fb2d14556889f4fd9014ef9db
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555552B2
Reaction notes
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