Potassium Carbonate → HCID 68211507, compound

HRID 1025509Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)([OH:11])[CH3:10].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:9]1([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:11]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of tert-butyl 4-(1-(2-bromophenyl)-2-hydroxypropan-2-yl)piperidine-1-carboxylate (1.14 g, 2.86 mmol), BINAP (0.266 g, 0.427 mmol), Pd(OAc)2 (93 mg, 0.412 mmol), and K2CO3 (1.188 g, 8.59 mmol) in toluene (14.3 mL) was degassed for 10 min. After this time, the reaction mixture was heated in 110° C. oil bath overnight. At the conclusion of this period, the resulting solid was collected by filtration and rinsed with CH2Cl2. The filtrate was concentrated to afford the crude product, which was purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 25% EtOAc) to afford Compound 11B as a colorless oil (0.959 g, 97% yield). LC/MS (m/z)=657 (2M+Na)+.

Workup

customwas degassed for 10 min
filtrationAt the conclusion of this period, the resulting solid was collected by filtration
washrinsed with CH2Cl2
concentrationThe filtrate was concentrated
customto afford the crude product, which
customwas purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 25% EtOAc)

Sources & evidence

ORD record: ord-e943117a63e241d7ab475dccd469beaf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729084B2

Reaction notes

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