1,4-Dioxaspiro[4.4]non-7-ene → 6-(2-Methylpropane-2-sulfonyl)-6-azaspiro[bicyclo[3.1.0]hexane-3,2'-[1,3]dioxolane]

HRID 1750555Notes

Reaction equation

HRID 1750555 reaction equation
[O:1]1[C:5]2([CH2:9][CH:8]=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl[N:11]([Na])[S:12]([C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:14])=[O:13].[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>C(#N)C>[CH3:16][C:15]([S:12]([N:11]1[CH:8]2[CH:7]1[CH2:6][C:5]1([CH2:9]2)[O:4][CH2:3][CH2:2][O:1]1)(=[O:14])=[O:13])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 130147471,4-Dioxaspiro[4.4]non-7-eneHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 178455662HCID 178455662, compound2×

Product 1

HCID 1183083266-(2-Methylpropane-2-sulfonyl)-6-azaspiro[bicyclo[3.1.0]hexane-3,2'-[1,3]dioxolane]

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,4-dioxaspiro[4.4]non-7-ene (370 mg, 2.93 mmol) and N-chloro-2-methyl-N-sodiopropane-2-sulfonamide (Intermediate 43; 965 mg, 4.99 mmol) in acetonitrile (16 ml) was added trimethylphenylammonium tribromide (CAS number 4207-56-1; 110 mg, 0.29 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature for 2 hours then heated to 40° C. for 18 hours. The reaction mixture was filtered through a plug of silica, washed with diethyl ether and the filtrate concentrated in vacuo. The crude material was purified column chromatography (silica, 0-50% diethyl ether/petroleum) to afford the title compound.

Workup

  1. temperaturethen heated to 40° C. for 18 hours
  2. filtrationThe reaction mixture was filtered through a plug of silica
  3. washwashed with diethyl ether
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe crude material was purified column chromatography (silica, 0-50% diethyl ether/petroleum)

Sources & evidence

ORD record
ord-3deb1f0332fe4be4b6291a6c13ff72bc
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…