Diethyl Ether → Tert-butyl 2-methoxy-4-methylpyridin-3-ylcarbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([O:15][CH3:16])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]COCC.CN(CCN(C)C)C.[Li]CCCC.IC>>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([O:15][CH3:16])=[N:11][CH:12]=[CH:13][C:14]=1[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
6
Conditions
- Temperature
- -10 °C
Procedure
To a stirred solution of 1.12 g (5 mmol) of 3-(tert-butoxycarbonylamino)-2-methoxypyridine in 25 mL of dry ether containing 1.8 mL, (12 mmol) of TMEDA at -78° C. under an argon atmosphere was added 4.8 mL (12 mmol) of a 2.5M solution of nBuLi in hexanes. The mixture was then warmed to -10° C. for 2 h. Recooling to -78° C. and treatment with iodomethane (0.99 g, 7 mmol) followed by warming to room temperature for 1 h produced the desired product which was purified by quenching with water, washing the ether layer with 0.1N HCl, drying (MgSO4), concentration and flash chromatography (9:1 hexanes:EtOAc). Yield: 1.00 g (84%). Recrystallization from heptane provided further purification. m.p.: 93°-95° C.
Workup
- customRecooling to -78° C.
- temperatureby warming to room temperature for 1 h
Sources & evidence
- ORD record
- ord-464c93e213e845d1a1af1f2b772bcfb8
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05532358
Reaction notes
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