Dichloromethane → HCID 70171495, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][Si](C(C)(C)C)(C)C)[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+].C(Cl)Cl>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:24])[CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of (R)-3-(tert-butoxycarbonylamino)-1-[7-(tert-butyldimethylsilyloxy)naphthalen-1-yl]pyrrolidine, as described above in Step H, (970 mg, 2.19 mmol) in THF (15 mL) was added TBAF (2.40 mL of a 1 M solution in THF, 2.40 mmol), dropwise. The mixture was stirred at ambient temperature for 30 min, then poured into saturated aqueous NaHCO3 (50 mL) and CH2Cl2 (100 mL). The aqueous layer was extracted further with CH2Cl2 (2×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of CH2C2—0% to 20% EtOAc to yield the desired phenol.
Workup
- extractionThe aqueous layer was extracted further with CH2Cl2 (2×50 mL)
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography on silica
- washeluting with a gradient of CH2C2—0% to 20% EtOAc
Sources & evidence
- ORD record
- ord-5c65338dcb3b423cb5e26175c8d3145d
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06441017B1
Reaction notes
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