Diisopropylethylamine → tert-Butyl [(3R,4R,5S)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methyl-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate

HRID 1499500Notes

Reaction equation

I[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[O:11][CH2:12][CH2:13][C:3]=12.[Si:14]([O:21][C@@H:22]1[C@@H:27]([CH3:28])[CH2:26][NH:25][CH2:24][C@H:23]1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CCO>[Si:14]([O:21][C@@H:22]1[C@@H:27]([CH3:28])[CH2:26][N:25]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]3[O:11][CH2:12][CH2:13][C:3]=23)[CH2:24][C@H:23]1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4-iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine (110.4 mg, 0.3780 mmol) and tert-butyl ((3R,4R,5S)-4-{[tert-butyl(dimethyl)silyl]oxy}-5-methylpiperidin-3-yl)carbamate (from Example 28, Step 7, 100.0 mg, 0.2902 mmol) was added EtOH (2.0 mL) followed by DIPEA (163.8 mg, 1.267 mmol). The reaction mixture was heated at 100° C. for 15 h, and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-50% EtOAc in hexanes) to afford the sub-title compound as a yellow solid (118.2 mg, 80%). LCMS calc. for C24H41N4O6Si (M+H)+: m/z=509.3. found 509.3.

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ec6b2b46a9ad4b40bced80ab15b1433d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200004B2

Reaction notes

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