Morpholine → HCID 67284582, compound

HRID 1618791Notes

Reaction equation

CC(C)([O-])C.[Na+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:48]1[CH:56]=[C:55]2[C:51]([C:52]3([CH2:69][O:68][C:67]([CH3:71])([CH3:70])[O:66][CH2:65]3)[C:53](=[O:64])[N:54]2C(OC(C)(C)C)=O)=[CH:50][CH:49]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:70][C:67]1([CH3:71])[O:66][CH2:65][C:52]2([C:51]3[C:55](=[CH:56][C:48]([N:7]4[CH2:12][CH2:11][O:10][CH2:9][CH2:8]4)=[CH:49][CH:50]=3)[NH:54][C:53]2=[O:64])[CH2:69][O:68]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a microwave vessel was added sodium tert-butoxide (0.19 g, 1.99 mmol), morpholine (0.13 mL, 1.49 mmol), XPhos (0.095 g, 0.20 mmol), Pd2(dba)3 (0.091 g, 0.099 mmol), and tert-butyl 6′-bromo-2,2-dimethyl-2′-oxospiro[[1,3]dioxane-5,3′-indoline]-1′-carboxylate (0.41 g, 0.99 mmol) in 1,4-dioxane (9.9 mL). The mixture was deoxygenated with argon for 5 min and stirred at 110° C. for 90 min under microwave irradiation. The resulting mixture was purified by column chromatography (eluting with a gradient of 10-70% EtOAc in hexanes) to give 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indolin]-2′-one as a white solid. Mass Spectrum (ESI) m/e=319.2 (M+1).

Workup

customThe mixture was deoxygenated with argon for 5 min
customThe resulting mixture was purified by column chromatography (
washeluting with a gradient of 10-70% EtOAc in hexanes)

Sources & evidence

ORD record: ord-eabb8125a4cd4fe1babf157bf49a35cf
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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