1,4-Dioxaspiro[4.5]decan-8-one → 8-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1025768Notes

Reaction equation

[SnH3][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:13]1[C:17]2([CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]2)[O:16][CH2:15][CH2:14]1>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[C:20]1([OH:23])[CH2:21][CH2:22][C:17]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:18][CH2:19]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-stannyl pyrimidine (200 mmol, 80 g), prepared as previously described in the literature (Tetrahedron, 1994, 50, 275-284), in THF (1 L) was added n-butyllithium (240 mmol, 150 mL) at −78° C. The reaction was stirred for 30 min at −78° C. and 1,4-dioxa-spiro[4.5]decan-8-one (200 mmol, 30 g) was added. The reaction was allowed to stir overnight while warming to ambient temperature. The reaction was then quenched using NH4Cl and extracted using EtOAc (3×400 mL). The organic layers were combined and dried over MgSO4 and concentrated in vacuo. The crude was taken to the next step.

Workup

stirringto stir overnight
temperaturewhile warming to ambient temperature
customThe reaction was then quenched
extractionextracted
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b4caa8034f4841e9b58831922ba3357a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729063B2

Reaction notes

Loading…