Water → HCID 69026499, compound

HRID 1433096Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:14][CH2:13]1)=O)C.O>C1COCC1.O.[OH-].[Na+]>[CH3:25][O:24][C:21]1[N:20]=[CH:19][C:18]([N:15]2[CH2:16][CH2:17][CH:12]([CH2:10][OH:9])[CH2:13][CH2:14]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottom flask is charged with anhydrous THF (8 mL) and LAH (122 mg, 3.17 mmol) is added. The contents are placed under N2 and cooled to 0° C. To this is added a solution of 6′-methoxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-carboxylic acid ethyl ester (400 mg, 1.51 mmol) in THF (2 ml) over 5 min. The reaction is allowed to come to r.t. and continue to stir for an additional hour. 4 drops of H2O are added, followed by 4 drops of 15% NaOH(aq) and allowed to stir at r.t. for 20 min. 0.5 mL of H2O are added, and the contents are filtered through a pad of celite and washed with THF. The solution is reduced to an oil under vacuum, and purified by flash chromatography on silica gel using 3% methanol/methylene chloride as the eluent to provide (6′-methoxy-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-4-yl)-methanol. 1H NMR (300 MHz, CDCl3) δ 7.95 (d, 1H), 7.29 (dd, 1H), 6.66 (d, 1H), 3.88 (s, 3H), 3.53 (m, 4H), 2.65 (dt, 2H), 1.85 (m, 2H), 1.65 (m, 1H), 1.42 (m, 2H); MS (EI) 222 (M)+.

Workup

additionis added
customto come to r.t.
stirringto stir at r.t. for 20 min
filtrationthe contents are filtered through a pad of celite
washwashed with THF
custompurified by flash chromatography on silica gel using 3% methanol/methylene chloride as the eluent

Sources & evidence

ORD record: ord-e2dc87f7d95a4594babacfc97843f0b7
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

Loading…