1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

HRID 1431990Notes

Reaction equation

O[C@H:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=[O:13])[CH:5]=[CH:4][C:3]1=2.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([C@@H:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([CH:12]=[O:13])[CH:5]=[CH:4][C:3]1=2)=[N+:29]=[N-:30]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-5-Hydroxy-5,6,7,8-tetrahydronapthalene-2-carbaldehyde (19.73 mmol) was dissolved in 50 mL of toluene and cooled to 0° C. Diphenylphosphoryl azide (29.6 mmol, 1.5 eq) was added, followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (23.07 mmol, 1.2eq). After stirring at room temperature overnight, the solvent was evaporated. The residue was purified by SiO2 chromatography (5-30% ethyl acetate in dichloromethane) to afford the title compound. MS (m/z): 204.2 (M+H).

Workup

customthe solvent was evaporated
customThe residue was purified by SiO2 chromatography (5-30% ethyl acetate in dichloromethane)

Sources & evidence

ORD record: ord-3182dd554647409aac6941f83c79fe94
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612060B2

Reaction notes

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