1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-azido-3,4-dihydro-2H-pyrano[2,3-b]pyridine

HRID 1363176Notes

Reaction equation

C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:18]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH:21](O)[CH2:20][CH2:19]1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>[N:15]([CH:21]1[C:22]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[O:18][CH2:19][CH2:20]1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 0 °C

Procedure

(Prep ref: Phompson, A. S. et. al. J. Org. Chem., 1993, 58, 5886-5888). Diphenyl phosphoryl azide (0.81 mL) was added to a suspension of 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol (0.37 g) in dry toluene (10 mL) then the mixture was cooled to 0° C. under an Ar atmosphere. Neat DBU (0.56 mL) was added and the resultant biphasic mixture was stirred at 0° C. for 2 hr and then at RT for 15 hr. The biphasic solution was diluted with sat. NaHCO3 and extracted with DCM (2×). The combined organics were concentrated and purified by silica gel chromatography using 10, 25 and 50% EtOAc/Hex elutants to afford the titled product (0.31 g) NMR CDCl3 1H δ 8.2 (dd, 1H), 7.6 (dd, 1H), 7.0 (dd, 1H), 4.7 (dd, 1H), 4.4 (m, 2H), 2.2 (m, 1H), 2.1 (m, 1H); MH+=177.

Workup

waitat RT for 15 hr
extractionextracted with DCM (2×)
concentrationThe combined organics were concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-e774a1c8d496409ba332ef70ea96d6ea
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884109B2

Reaction notes

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