Imidazole → tert-Butyl 6-(tert-butyldimethylsilyloxy)hexylcarbamate
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>C(Cl)Cl>[Si:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl 6-hydroxyhexylcarbamate (21 mmol) in CH2Cl2 (30 ml) was added imidazole (27 mmol) at 0° C. The reaction mixture was kept at 25° C. and stirred for 20 min, then cooled to 0° C. To the resulting reaction mixture was added tert-butyldimethylchlorosilane (23 mmol) dropwise over 30 min at 0° C. The reaction mixture was allowed to warm to 25° C. and stirred for 16 h and then filtered. The filtrate was washed with 1 N HCl (2×25 ml) and brine (30 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by SiO2 flash column (eluent: petroleum ether and then CH2Cl2). Yield 6.53 g (87% yield).
Workup
- customwas kept at 25° C.
- customTo the resulting reaction mixture
- temperatureto warm to 25° C.
- stirringstirred for 16 h
- filtrationfiltered
- washThe filtrate was washed with 1 N HCl (2×25 ml) and brine (30 ml)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by SiO2 flash column (eluent
Sources & evidence
- ORD record
- ord-b9f519400d5e4537b17781dabf7aa039
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716293B2
Reaction notes
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