Tert-Butyl hypochlorite → HCID 56966449, compound

HRID 1770773Notes

Reaction equation

HRID 1770773 reaction equation
[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][N:4]1[C:8](=[O:9])[C:7]([CH3:11])([CH3:10])[NH:6][C:5]1([CH3:13])[CH3:12].C(O[Cl:21])(C)(C)C>CO>[Cl:21][N:6]1[C:7]([CH3:10])([CH3:11])[C:8](=[O:9])[N:4]([CH2:3][CH:2]([OH:1])[CH2:14][OH:15])[C:5]1([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508091HCID 67508091, compound

Product 1

HCID 56966449HCID 56966449, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(2,3-dihydroxypropyl)-2,2,5,5-tetramethylimidazolidin-4-one (250 mg, 1.2 mmol) in methanol (150 ml) was added tert-butylhypochlorite (150 mg, 1.4 mmol). The mixture was stirred for 1 hour at 0° C. The reaction mixture was concentrated in vacuo, and crude material is purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane) to give 256 mg (88%) of the title compound. 1H NMR (400 MHz, D2O) δ 4.06-3.98 (m, 1H), 3.62 (dd, J=12.0, 4.0 Hz, 1H), 3.56-3.44 (m, 2H), 3.36 (dd, J=14.8, 8.4 Hz, 1H), 1.54 (s, 6H), 1.38-1.37 (m, 6H). 13C NMR (100 MHz, D2O) δ 175.5, 83.9, 69.4, 66.0, 63.4, 43.6, 24.2, 23.9, 22.72, 22.4. LRMS (ESI/APCI) m/z 251 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and crude material
  2. customis purified by silica gel flash chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3fbc29d21bd24cd08ee71558b1d2e237
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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