Potassium Carbonate → (R)-3-(4-Hydroxy-4-methyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 69512Notes

Reaction equation

[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][C@H:18](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CN1C(=O)CCC1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C(OCC)(=O)C.CN(C=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][C@@H:18]([N:5]2[CH2:6][CH2:7][C:2]([OH:8])([CH3:1])[CH2:3][CH2:4]2)[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 4-Methyl-piperidin-4-ol (2.2 g) and (S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (5.0 g) in acetonitrile (54 mL)/NMP (30 mL)/DMF (5 mL) was added potassium carbonate (9.2 g). The mixture was stirred at 80° C. for 12 h. Ethyl acetate and water was added. The aqueous phase was acidified, extracted with ethyl acetate. The collected organic phase were washed with water, dried over sodium sulfate and concentrated. The product with the molecular weight of 284.40 (C15H28N2O3) was obtained in this way; MS (ESI): 285 (M+H+).

Workup

extractionextracted with ethyl acetate
washThe collected organic phase were washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe product with the molecular weight of 284.40 (C15H28N2O3) was obtained in this way

Sources & evidence

ORD record: ord-71b392faa4a8405a8eaf090bbf4f2c68
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Reaction notes

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