Acetonitrile → 3-(3-(Bicyclo[2.2.1]heptan-2-ylmethoxy)phenyl)-3-hydroxypropanenitrile

HRID 875521Notes

Reaction equation

HRID 875521 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].[C:18](#[N:20])[CH3:19]>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:13]([OH:14])[CH2:19][C:18]#[N:20])[CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 795519583-(Bicyclo[2.2.1]heptan-2-ylmethoxy)benzaldehyde

Product 1

HCID 673166563-(3-(Bicyclo[2.2.1]heptan-2-ylmethoxy)phenyl)-3-hydroxypropanenitrile

Procedure

Addition of acetonitrile to 3-(bicyclo[2.2.1]heptan-2-ylmethoxy)benzaldehyde following the procedure given for Example 4 gave 3-(3-(bicyclo[2.2.1]heptan-2-ylmethoxy)phenyl)-3-hydroxypropanenitrile as a colorless oil. Yield (1.09 g, quant.). 1H NMR (400 MHz, DMSO-d6) δ 7.19-7.24 (m, 1H), 6.90-6.97 (m, 2H), 6.77-6.83 (m, 1H), 5.88 (d, J=4.5 Hz, 1H), 4.80-4.85 (m, 1H), 3.91 (dd, J=7.0, 9.8 Hz, 1H), 3.78-3.84 (m, 1H), 3.54-3.61 (m, 1H), 2.74-2.89 (m, 2H), 2.15-2.28 (m, 3H), 1.68-1.75 (m, 1H), 1.40-1.51 (m, 2H), 1.24-1.38 (m, 3H), 0.70-0.75 (m, 1H).

Sources & evidence

ORD record
ord-529486fc893f4b2dafba3d5658236876
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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