2-Bromoethanol → HCID 58180901, compound

HRID 1772807Notes

Reaction equation

HRID 1772807 reaction equation
Br[CH2:2][CH2:3][OH:4].[CH3:5][C@H:6]1[NH:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:4][CH2:3][CH2:2][N:11]1[CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][C@H:6]1[CH3:5]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2756811(R)-1-Boc-3-methylpiperazine

Product 1

HCID 58180901HCID 58180901, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Bromoethanol (1.1 mL, 15 mmol) was added to a mixture of tert-butyl (3R)-3-methylpiperazine-1-carboxylate (2.0 g, 10 mmol, Aldrich) and potassium carbonate (4.1 g, 30 mmol) in acetonitrile (35 mL). The mixture was heated to reflux for 10 hours, cooled to room temperature, filtered and concentrated. Flash column chromatography, eluting with a gradient from 0-10% ethyl acetate/hexanes, afforded product as a colorless oil (1.40 g, 57%). 1H NMR (300 MHz, CDCl3): δ 3.70-2.85 (m, 5H), 2.80 (ddd, 1H), 2.59-2.46 (m, 1H), 2.39-2.20 (m, 2H), 1.75-1.55 (m, 2H), 1.46 (s, 9H), 1.04 (d, 3H); LCMS (M+H)+: 245.2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washFlash column chromatography, eluting with a gradient from 0-10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-929e87c7adb24afb8b03e6e8e53a1b1b
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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