Trimethylsilyl iodide → (3S,6R)-3-amino-6-(tert-butyl-dimethyl-silanyloxy)-1-pyridin-3-ylmethyl-azepan-2-one

HRID 2224020Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:11][N:10]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:9]1=[O:30])(C)(C)C.C[Si](I)(C)C>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:11][N:10]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:9]1=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of [(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-2-oxo-1-pyridin-3-ylmethyl-azepan-3-yl]-carbamic acid tert-butyl ester (5.0 g, 11.1 mmol) in CH2Cl2 (50 mL) at −78° C. is added trimethylsilyl iodide (2.8 g, 14.0 mmol) neat. After 30 min the reaction solution is warmed to 0° C. and stirred for 15 min. The reaction is quenched with a solution of CH3OH (25 mL) and NH4HCO3 (10 mL, saturated in H2O), and partitioned with H2O/CH2Cl2. The CH2Cl2 fraction is dried over Na2SO4 and evaporated to a gum and chromatographed on silica (95% CH2Cl2/5% CH3OH) to give 3.6 g (92.6%) of (3S,6R)-3-amino-6-(tert-butyl-dimethyl-silanyloxy)-1-pyridin-3-ylmethyl-azepan-2-one as a white solid. MS (ESI) 350.2 (M+H)+

Workup

customThe reaction is quenched with a solution of CH3OH (25 mL) and NH4HCO3 (10 mL, saturated in H2O)
custompartitioned with H2O/CH2Cl2
dry with materialThe CH2Cl2 fraction is dried over Na2SO4
customevaporated to a gum
customchromatographed on silica (95% CH2Cl2/5% CH3OH)

Sources & evidence

ORD record: ord-02379aae9dd446a3a86beb809d56365a
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378410B2

Reaction notes

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