Water → 1-Methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane

HRID 1750501

Reaction equation

HRID 1750501 reaction equation
[CH3:1][C:2]1[CH2:6][CH2:5][CH2:4][CH:3]=1.Cl[N-:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Na+].[Br-].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.O>C1COCC1>[CH3:1][C:2]12[N:8]([S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)(=[O:10])=[O:11])[CH:6]1[CH2:5][CH2:4][CH2:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 127461-MethylcyclopenteneHCID 3641960Chloramine-THCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 1180245801-Methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-methylcyclopent-1-ene (CAS number 693-89-0; 50.0 g, 609.75 mmol) iii and sodium chloro(4-methylbenzenesulfonyl)azanide (CAS number 127-65-1; 192 g, 680.85 mmol) in THF (2500 ml) was added trimethylphenylammonium tribromide (13.3 g, 61.57 mmol). The reaction was stirred vigorously at 25° C. for 12 hours. The reaction mixture was poured into water (1500 ml) and the organics were extracted with ethyl acetate (3×1000 ml). The combined organics were washed with water (500 ml), brine (500 ml), dried over sodium sulfate and concentrated in vacuo. This was then purified by column chromatography (silica, 0-2.5% ethyl acetate/n-hexane) to afford the title compound.

Workup

  1. extractionthe organics were extracted with ethyl acetate (3×1000 ml)
  2. washThe combined organics were washed with water (500 ml), brine (500 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThis was then purified by column chromatography (silica, 0-2.5% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3662870c197c4417a45b083481a04d69
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Linked notes

Loading…