Tert-butyl 2-(4-bromo-3-fluorophenyl)morpholine-4-carboxylate → HCID 89689576, compound

HRID 710253Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[C:16]([F:21])[CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cu][C:23]#[N:24]>C(OC)(C)(C)C>[C:23]([C:17]1[CH:18]=[CH:19][C:14]([CH:10]2[O:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)=[CH:15][C:16]=1[F:21])#[N:24]

Participants

Conditions

Temperature: 180 °C

Procedure

To a 20 mL microwave vial were added 2-(4-bromo-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (1.5 g, 4.16 mmol) N-methyl-pyrrolidone (10 ml) and copper(I)-cyanide (559 mg, 6.25 mmol). The vial was capped and heated in a microwave synthesizer (Personal Chemistry Emrys Optimizer) at 180° C. for 30 min. The reaction mixture was poured into tert-butylmethylether (150 ml) and extracted with brine (3×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 70% ethyl acetate in heptane) to yield a yellow solid (101 mg, 8%), MS (ISP): 307.2 ([M+H]+).

Workup

customThe vial was capped
extractionextracted with brine (3×50 mL)
dry with materialThe organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 50 g, 0% to 70% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-b5255673be314ef69e03dfbd347b2692
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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