Tert-Butyl hypochlorite → HCID 53232453, compound

HRID 1770775Notes

Reaction equation

HRID 1770775 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[NH:8][C:7]1([CH3:15])[CH3:14].C(O[Cl:21])(C)(C)C>CO>[Cl:21][N:8]1[C:9]([CH3:13])([CH3:12])[C:10](=[O:11])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][OH:1])[C:7]1([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 67508361HCID 67508361, compound

Product 1

HCID 53232453HCID 53232453, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(4-hydroxybutyl)-2,2,5,5-tetramethylimidazolidin-4-one, (622 mg, 2.9 mmol) in methanol (80 ml) was added tert-butylhypochlorite (473 mg, 4.4 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 15% methanol in dichloromethane) to give 213 mg (30%) of the title compound. 1H NMR (400 MHz, D2O) δ 3.74-3.66 (m, 2H), 3.34-3.30 (m, 2H), 2.08 (s, 1H), 1.78-1.71 (m, 2H), 1.65-1.57 (m, 2H), 1.47 (s, 6H), 1.36 (s, 6H). 13C NMR (100 MHz, D2O) δ 173.0, 82.3, 65.5, 62.5, 40.5, 29.8, 26.1, 25.5, 23.8. LRMS (ESI/APCI) m/z 249 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, and crude material
  2. customis purified by silica gel flash chromatography (0 to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5f78b267c8b04b4693902699cca6ee0e
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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