2-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonate → tert-BUTOXYCARBONYL-2(R/S)-[2-(1H-IMIDAZOL-1-YL)ETHYL]PIPERIDINE

HRID 392503Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[Na]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

The title compound from Step B above (2.68 g, 8.72 mmoles) (crude product, prior to chromatography) was dissolved in anhydrous DMF (30 mL) and sodium imidazole (1.18 g, 13.1 mmoles) was added. The mixture was heated at 70° C. for 2 h and then evaporated to dryness. The product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant to give the title compound (1.69 g, 69%): ESMS: m/z 280.1 (MH+); dH (CDCl3) 1.48 ppm (9H, s, CH3); dC (CDCl3) CH3: 28.5, 28.5, 28.5; CH2: 19.1, 25.5, 28.9, 31.8, ˜39.1, 44.3; CH: 48.1, 118.9, 129.5, 137.1; C: 80.1, carbonyl not visible.

Workup

customevaporated to dryness
customThe product was directly chromatographed on silica gel using 1% (10% conc. NH4OH in methanol)-dichloromethane as the eluant

Sources & evidence

ORD record: ord-06cec6602d824474b50d5a35adbad18b
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800636B2

Reaction notes

Loading…