1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(1S)-1-azidoethyl]-2-bromobenzene

HRID 605337Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C@H:4](O)[CH3:5].C1(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1COCC1>[N:25]([C@H:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[Br:1])[CH3:5])=[N+:26]=[N-:27]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-(+)-2-bromo-α-methylbenzyl alcohol (402 mg, 2.0 mmol) and diphenylphosphoryl azide (0.692 ml, 3.2 mmol) in THF (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.466 ml, 3.2 mmol). The mixture was heated at 50° C. for overnight, partitioned with H2O and AcOEt, and then adjusted to pH 7 by adding 1M HCl. The organic layer was dried with MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography [eluting with n-hexane/AcOEt=95/5] to give the title compound (381 mg, 84%).

Workup

custompartitioned with H2O and AcOEt
additionby adding 1M HCl
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
customevaporated
customThe residue was purified by silica gel column chromatography [eluting with n-hexane/AcOEt=95/5]

Sources & evidence

ORD record: ord-ec58cfed91f841eca9efb9fef661d3c4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

Loading…