Tert-Butyl hypochlorite → HCID 46202013, compound

HRID 1023474Notes

Reaction equation

HRID 1023474 reaction equation
[Cl-:1].[CH3:2][N+:3]1([CH3:14])[CH2:13][CH2:12][C:6]2([O:10][C:9](=[O:11])[NH:8][CH2:7]2)[CH2:5][CH2:4]1.C(O[Cl:20])(C)(C)C>CO>[Cl-:20].[Cl:1][N:8]1[CH2:7][C:6]2([CH2:12][CH2:13][N+:3]([CH3:2])([CH3:14])[CH2:4][CH2:5]2)[O:10][C:9]1=[O:11]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 46202673HCID 46202673, compound

Product 1

HCID 46202013HCID 46202013, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8,8-Dimethyl-2-oxo-1-oxa-3-aza-8-azoniaspiro[4.5]decane chloride (1.60 g, 7.25 mmol) was dissolved in methanol (80 ml). t-Butylhypochlorite (1.18 g, 10.87 mmol) was added to the solution, and the combined mixture was stirred for 1 hour at room temperature. The reaction mixture was monitored by HPLC-MS. The reaction mixture was concentrated in vacuo. The crude material was purified by Prep-HPLC to give 243 mg (13%). 1H NMR (CDCl3) δ 3.84 (s, 2H), 3.52-3.69 (m, 4H), 3.25 (s, 3H), 3.18 (s, 3H), 2.32-2.46 (m, 4H); MS(ESI+) calculated for C9H16ClN2O2: 219.09, Found: 219 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude material was purified by Prep-HPLC
  3. customto give 243 mg (13%)

Sources & evidence

ORD record
ord-f0053a6c595e4533876feead5abd6973
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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