Sodium Chloride → HCID 21112788, compound

HRID 2284736Notes

Reaction equation

[C:1]([C:3]1(C(O)=O)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:19])=CC=1.C([N:31]([CH2:34]C)CC)C.[Cl-].[Na+].[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1([NH:31][C:34](=[O:19])[O:42][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-cyanotetrahydro-2H-pyrane-4-carboxylic acid (1.69 g) synthesized according to the method described in Journal of the American Chemical Society, 1942, vol. 64, p. 1672 in tetrahydrofuran (20 mL) and tert-butanol (80 mL), diphenylphosphonyl azide (2.32 mL) and triethylamine (1.51 mL) were added at room temperature, and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and saturated aqueous sodium chloride were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl (4-cyanotetrahydro-2H-pyran-4-yl)carbamate (G14, 1.38 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-2bdd8323735248a2816fc5c6a8beb917
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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