Tert-Butyl hypochlorite → HCID 54582542, compound

HRID 1770746Notes

Reaction equation

HRID 1770746 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH:7][C:6]([CH3:13])([CH3:12])[C:5]1=[O:14].C(O[Cl:20])(C)(C)C>CO>[Cl:20][N:7]1[C:8]([CH3:10])([CH3:11])[CH2:9][N:4]([CH2:3][CH2:2][OH:1])[C:5](=[O:14])[C:6]1([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 21951121HCID 21951121, compound

Product 1

HCID 54582542HCID 54582542, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(2-hydroxyethyl)-3,3,5,5-tetramethylpiperazin-2-one (125 mg, 0.63 mmol) in methanol (1 ml) was cooled to 0° C. tert-Butylhypochlorite (106 ul, 0.94 mmol) was added. The resulting solution was stirred for 60 minutes, and then concentrated under reduced pressure. The crude material was purified by column chromatography eluting from silica gel with a gradient of 0-8% methanol in dichloromethane to give 111 mg of a white solid. 1H NMR (D2O, 400 MHz) δ 1.21 (s, 3H), 1.43 (s, 3H), 3.36 (s, 2H), 3.43-3.345 (t, J=5.6 Hz, 2H), 3.64-3.66 (t, J=5.6 Hz, 2H). 13C NMR (D2O, 100 MHz) δ 172.9, 68.1, 60.0, 58.4, 57.4, 49.6, 25.5, 22.7. LRMS (ESI/APCI) m/z 235 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by column chromatography
  4. washeluting from silica gel with a gradient of 0-8% methanol in dichloromethane

Sources & evidence

ORD record
ord-ac061659e0a7400893080feea8439cac
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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