Ethanol → HCID 69742791, compound

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].[BH4-].[Na+].C([OH:35])C>>[CH2:29]([O:28][C:26]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:9][C:8](=[O:35])[N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:27])[CH3:30]

Participants

Reactant 3

HCID 702Ethanol

HCID 4311764Sodium borohydride

HCID 86588174HCID 86588174, compound

Product 1

HCID 69742791HCID 69742791, compoundYield 80%

Procedure

To a solution of 1-[6-(4-formyl-phenoxy)-pyridin-3-yl]-pyrolidine-2,2-dicarboxylic acid diethyl ester (1.0 g, 2.3 mmol) in 30 mL of ethanol was added sodium borohydride (0.090 g, 2.3 mmol) at 0° C. After stirring for 3 hours, the mixture was concentrated in vacuo, diluted with ethyl acetate and water, and the aqueous layer was cautiously acidified with 1M hydrochloric acid, then neutralized with saturated aqueous sodium bicarbonate. The mixture was extracted three times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo, affording 0.80 g (80%) of 1-[6-(4-hydroxymethyl-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup. 1H NMR (CDCl3, 400 MHz): 8.04 (d, 1H, J=2.4 Hz), 7.72 (dd, 1H, J=2.4, 8.8 Hz), 7.40 (d, 2H, J=8.8 Hz), 7.12 (d, 2H, J=8.4 Hz), 6.91 (d, 1H, J=8.8 Hz), 4.70 (s, 2H), 4.19 (q, 4H, J=7.6 Hz), 2.75 (m, 2H), 2.65 (m, 2H), 1.18 (t, 6H, J=7.2 Hz) ppm. MS (APCl, m/z): 429.1 [M+H]+.