Water → HCID 46198683, compound

HRID 2061079Notes

Reaction equation

HRID 2061079 reaction equation
[ClH:1].[CH3:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:7][C:8]([CH3:20])([CH3:19])[CH2:9][CH2:10][N+:11]12[CH2:18][CH2:17][CH:14]([CH2:15][CH2:16]1)[CH2:13][CH2:12]2.C(O[Cl:26])(C)(C)C.O>CO>[CH3:2][S:3]([O-:6])(=[O:5])=[O:4].[Cl:1][N:7]([Cl:26])[C:8]([CH3:20])([CH3:19])[CH2:9][CH2:10][N+:11]12[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18]1)[CH2:15][CH2:16]2

Participants

5

Reactant 3

HCID 962WaterHCID 521297Tert-Butyl hypochloriteHCID 87350747HCID 87350747, compound

Product 1

HCID 46198683HCID 46198683, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3-amino-3-methylbutyl)-1-azoniabicyclo[2.2.2]octane methanesulfonate hydrochloride (0.31 g, 1.2 mmol) in methanol (4.5 mL) was cooled in an ice bath for 15 min. t-BuOCl (0.41 mL, 3 equiv, 3.48 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., and 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 concentrated via rotovap with the water bath set at 25° C. to give a white solid, (0.21 g, 58.9%). 1H NMR (D2O, 400 MHz): δ 1.43 (s, 6H), 1.96-2.03 (m, 6H), 2.16-2.25 (m, 3H), 2.82 (s, 3 H), 3.21-3.29 (m, 2H), 3.40-3.46 (m, 6H). LRMS (ESI+) for C12H23Cl2N2+ (265.1); Found: 265, 267 (M+, M2H+).

Workup

  1. additionwas added in one portion via syringe to the colorless solution
  2. customto give a deep yellow solution
  3. concentrationconcentrated under reduced pressure
  4. customto yield a colorless oil
  5. custompurified via reverse phase chromatography on a Shimadzu Prep-LC
  6. customFractions were collected
  7. concentrationconcentrated via rotovap with the water bath
  8. customset at 25° C.
  9. customto give a white solid, (0.21 g, 58.9%)

Sources & evidence

ORD record
ord-377ba807465842cbb11f4e619d95773b
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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