Sodium Azide → tert-Butyl cis-5-azido-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate

HRID 602453Notes

Reaction equation

[OH:1][C:2]1([CH2:8][C@H:9]2[CH2:14][CH2:13][C@H:12](OS(C)(=O)=O)[CH2:11][N:10]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O>[N:27]([C@H:12]1[CH2:11][N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:9]([CH2:8][C:2]2([OH:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)[CH2:14][CH2:13]1)=[N+:28]=[N-:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of tert-butyl trans-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-[(methylsulfonyl)oxy]piperidine-1-carboxylate (673 mg, 1.71 mmol, step 3 of Example 2) in N,N-dimethylformamide (4 mL) was added sodium azide (334 mg, 5.13 mmol) at room temperature and the mixture was stirred at 80° C. for 24 h. After cooling, the mixture was quenched with water (50 mL), and extracted with ethyl acetate (50 mL×4). The combined organic layer was washed with water (50 mL×4), brine (30 mL), dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (2:1) to give 480 mg (82%) of the title compound as a white crystal.

Workup

temperatureAfter cooling
customthe mixture was quenched with water (50 mL)
extractionextracted with ethyl acetate (50 mL×4)
washThe combined organic layer was washed with water (50 mL×4), brine (30 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record: ord-5b80d1431fd2415a806670542be25074
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906532B2

Reaction notes

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