Ethanol → HCID 69742791, compound

HRID 1760372Notes

Reaction equation

HRID 1760372 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

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 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]+.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate and water
  3. extractionThe mixture was extracted three times with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-159f34c092d248a2a44d79918144143c
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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