Methanol → [4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-yl]-methanol

HRID 1959604Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=C)[C:3]=1[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[BH4-].[Na+].C[OH:21]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:21])[C:3]=1[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1

Participants

Conditions

Temperature: -50 °C

Procedure

4-Methyl-3-(tetrahydro-pyran-2-yloxymethyl)-2-vinyl-pyridine (300 mg. 1.29 mmol) was dissolved in DCM (36 mL) and cooled to −50° C. A gentle flow of ozone was bubbled through the reaction mixture until the colour of the solution changed to slight blue. NaBH4 (486 mg. 12.9 mmol) dissolved in MeOH (15 mL) was added and the reaction was allowed to warm to RT over a period of 1 h. The solvents were removed in vacuo and the residue pardoned between water (20 mL) and EtOAc (20 mL) extracted with EtOAc (3×20 mL). The combined organic fractions were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 40:1→20:1) to give the title compound. MS (m/z): 238.0 [M+H+].

Workup

customA gentle flow of ozone was bubbled through the reaction mixture until the colour of the solution
additionwas added
temperatureto warm to RT over a period of 1 h
customThe solvents were removed in vacuo
extractionextracted with EtOAc (3×20 mL)
washThe combined organic fractions were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel (elution with DCM/MeOH 40:1→20:1)

Sources & evidence

ORD record: ord-5c3f58b4766547e6866a9d01f809a2c3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410134B2

Reaction notes

Loading…