Tert-Butyl hypochlorite → HCID 46198844, compound
Reaction equation
[ClH:1].[Cl-:2].[NH2:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][N+:7]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C(O[Cl:20])(C)(C)C>CO.O>[Cl-:20].[Cl:1][N:3]([Cl:2])[C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][N+:7]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(3-amino-3-methylbutyl)-1-methylpyrrolidinium chloride hydrochloride (1.07 g, 4.4 mmol) in a mixture of methanol (15 mL) and water (10 mL) was cooled in an ice bath for 15 min. t-BuOCl (1.56 mL, 3 equiv, 13.2 mmol) was added in one portion via syringe to the colorless solution to give a deep yellow solution. The reaction mixture was stirred for 30 min at 0° C., then concentrated under reduced pressure to yield a colorless oil. This oil was dissolved into water and purified via reverse phase chromatography on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. Fractions were pooled and lyophilized to give a pale yellow foam, (0.94 g, 77.6%). 1H NMR (D2O, 400 MHz): δ 1.44 (s, 6H), 2.17 (m, 4H), 2.17-2.32 (m, 2H), 3.06 (s, 3 H), 3.45-3.60 (m, 6H). LRMS (ESI+) for C10H21Cl2N2+ (239.1); Found: 239, 241 (M+, M2H+).
Workup
- additionwas added in one portion via syringe to the colorless solution
- customto give a deep yellow solution
- concentrationconcentrated under reduced pressure
- customto yield a colorless oil
- custompurified via reverse phase chromatography on a Shimadzu Prep-LC
- customFractions were collected
- customto give a pale yellow foam, (0.94 g, 77.6%)
Sources & evidence
- ORD record
- ord-66c1d4acf72b4f8fb8163c302dbcd9b4
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278482B2
Reaction notes
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