Sodium Hydroxide → HCID 59253243, compound

HRID 1809413Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][CH2:9][C:10]([CH3:17])([CH3:16])[C:11](=O)[CH2:12][C:13]#[N:14])=[CH:5][CH:4]=1.[OH-:20].[Na+].S(O)(O)(=O)=O.[NH2:27]O>O>[CH3:16][C:10]([C:11]1[CH:12]=[C:13]([NH2:14])[O:20][N:27]=1)([CH3:17])[CH2:9][O:8][CH2:7][C:6]1[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 2.0 g (7.65 mmol) of 5-(4-methoxy-benzyloxy)-4,4-dimethyl-3-oxo-pentanenitrile and 0.62 g (15.40 mmol) of sodium hydroxide in water (40 mL) are added 0.64 g (3.90 mmol) of hydroxylamine sulfate. The reaction is stirred at 100° C. for 18 h. After cooling to room temperature, the reaction is diluted with water and extracted with ethyl acetate (3×20 mL). The combined organic extracts are washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure. The residual oil is purified by flash column chromatography using Biotage SP1 (silica, eluent hexanes, 5-50% ethyl acetate) to yield 0.873 g of 3-[1,1-dimethyl-2-(4-methoxybenzyl-oxy)-ethyl]-isoxazol-5-ylamine as a pale yellow solid. Yield 41%, m/z 277 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29 (6H, s), 3.44 (2H, s), 3.81 (3H, s), 4.35 (2H, br. s), 4.46 (2H, br. s), 5.06 (1H, s), 7.22-7.27 (2H, m), 6.86-6.89 (2H, m).

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate (3×20 mL)
washThe combined organic extracts are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationThe filtrate is concentrated under reduced pressure
customThe residual oil is purified by flash column chromatography

Sources & evidence

ORD record: ord-a64e775d8111445b9e4c2b1041817e32
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362039B2

Reaction notes

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