Sodium Azide → 3-Azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

HRID 556153Notes

Reaction equation

HRID 556153 reaction equation
Br[CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:4]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:4]1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 248577553-Bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 248577563-Azidomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthaleneYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of compound 12 (0.293 g, 0.79 mmol) and sodium azide (0.154 g, 2.38 mmol) in DMF (5 ml) was stirred at 60° C. for 24 hours. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between water and EtOAc. The organic layer was separated, washed with water, dried over Na2SO4, and evaporated to give compound 13 as a pale yellow oil (mixture of cis and trans diastereomers, ratio=1:1.1, 0.18 g, 68%). The diastereomers were separated using a preparative chiral HPLC procedure (ChiralPak OD column; hexanes:MeOH=98:2; μ=8 ml/min; and λ=225 nm) to give compounds 13a-13d (retention times: 9.8 min, 12.0 min, 14.5 min and 20.1 min, respectively).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was partitioned between water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-68fc00bc44af4bccbf5a3729bb09eedb
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

Loading…