Cesium carbonate → HCID 66906112, compound

HRID 1689769Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH3:19].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][O:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][C:9]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[C:10]([CH3:19])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-hydroxypiperidine (2.65 g, 25.4 mmol), methyl 4-bromo-3-methylbenzoate (5.00 g, 21.8 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.37 g, 2.17 mmol), palladium acetate (0.247 g, 1.10 mmol), cesium carbonate (21.5 g, 65.3 mmol) in 1,4-dioxane (100 mL) is heated in a 350 mL pressure vessel for 18 h at 80° C. under nitrogen and then at 120° C. for 4 h. The mixture is filtered and concentrated under reduced pressure. The residue is purified on silica (120 g) using a gradient of 0 to 90% ethyl acetate in heptane to provide the title compound (2.4 g, 44%). LC-ES/MS m/z 250.2 (M+1)

Workup

filtrationThe mixture is filtered
concentrationconcentrated under reduced pressure
customThe residue is purified on silica (120 g)

Sources & evidence

ORD record: ord-9493f03af51e4f08ad24cc9127ddca8e
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153624B2

Reaction notes

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