Water → Tert-butyl 4-(4-aminoisothiazol-5-yloxy)piperidine-1-carboxylate

HRID 871037Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][S:7][C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)([O-])=O.O.C([O-])(O)=O.[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CO.C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[N:6][S:7][C:8]=1[O:9][CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of tert-butyl 4-(4-nitroisothiazol-5-yloxy)piperidine-1-carboxylate (1C3) (213 mg, 0.67 mmol) in methanol (4 mL) at room temperature was added water (3 mL), saturated NaHCO3 solution (3 mL) and Na2S2O4 (340 mg, 2 mmol). The mixture was stirred at 35° C. for 3 hours, cooled to room temperature, diluted with ethyl acetate (100 mL), washed with brine, dried over Na2SO4, and concentrated in vacuo at room temperature (25° C.). The residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether) to afford the product tert-butyl 4-(4-aminoisothiazol-5-yloxy)piperidine-1-carboxylate (1D4) (80 mg, 0.27 mmol).

Workup

temperaturecooled to room temperature
washwashed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo at room temperature (25° C.)
customThe residue was purified with flash column (eluent: 10-30% ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-ec200daa69da4d1da7b3e9fa9cf94aaa
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969584B2

Reaction notes

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