18-Crown-6 → HCID 86753720, compound
Reaction equation
Cl.[C:2]1([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:9]2[N:14]3[CH2:15][CH2:16][C@H:11]([C@H:12]([C:17]([OH:19])=[O:18])[CH2:13]3)[C@@H:10]2[OH:20])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.[CH:51]([C:54]1[CH:55]=[CH:56][C:57]([O:62][CH3:63])=[C:58]([CH:61]=1)[CH2:59]Br)([CH3:53])[CH3:52]>COCCOC>[C:21]1([CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@@H:9]2[N:14]3[CH2:15][CH2:16][C@H:11]([C@H:12]([C:17]([O:19][CH2:59][C:58]4[CH:61]=[C:54]([CH:51]([CH3:53])[CH3:52])[CH:55]=[CH:56][C:57]=4[O:62][CH3:63])=[O:18])[CH2:13]3)[C@@H:10]2[OH:20])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of (3S,4R,5S,6S)-6-diphenylmethyl-5-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylic acid hydrochloride (obtained in Example 1 (iii); 110 mg, 0.3 mmol) in DME (3 ml) was added potassium t-butoxide (130 mg, 1.2 mmol) followed by 18-crown-6 (300 mg, 1.2 mmol) at room temperature. To this solution was added 5-isopropyl-2-methoxybenzyl bromide (300 mg, 1.2 mmol) in DME (3 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour and at room temperature for 1 hour, quenched with H2O (10 ml), and extracted with CH2Cl2 three times. The combined extracts were dried over Na2SO4 and concentrated. The crude was purified by a column chromatography on silicagel to give a title compound (120 mg, 0.23 mmol, 78%).
Workup
- customquenched with H2O (10 ml)
- extractionextracted with CH2Cl2 three times
- dry with materialThe combined extracts were dried over Na2SO4
- concentrationconcentrated
- customThe crude was purified by a column chromatography on silicagel
Sources & evidence
- ORD record
- ord-59726778cfeb470eb6320389c6bf6cdd
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869499
Reaction notes
Loading…