4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → Tert-butyl 4-[2-(1-hydroxy-1-methyl ethyl)phenyl]piperidine-1-carboxylate

HRID 1627021Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12]C(C2C=CC=CC=2C(OC)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Mg]Br.[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:34]1[CH2:38][O:37]CC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:38]([OH:37])([CH3:34])[CH3:24])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (2.6 g, 8.14 mmol) [C.A.S. 732275-95-5] in THF (150 ml) cooled at 0° C. and under nitrogen atmosphere, was added dropwise methylmagnesium bromide −1.4 M solution in toluene/THF (17.443 ml, 24.421 mmol) and the resulting reaction mixture was stirred at 45° C. for 2 h. After cooling in an ice bath the mixture was carefully quenched with a saturated aqueous solution of ammonium chloride, and then extracted with EtOAc. The combined organic phase was dried (Na2SO4) and the solvent evaporated in vacuo to yield D28 (2.77 g, 69%)

Workup

customthe resulting reaction mixture
temperatureAfter cooling in an ice bath the mixture
customwas carefully quenched with a saturated aqueous solution of ammonium chloride
extractionextracted with EtOAc
dry with materialThe combined organic phase was dried (Na2SO4)
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-eca53d50dce04b119a85f58b2b7299ed
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785486B2

Reaction notes

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