Sodium borohydride → 2-(2-Biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester
Reaction equation
C([C@H]1COC(C)(C)N1C(=O)C(C1C=CN(C2C=CC(C3C=CC=CC=3)=CC=2)C=1)O)C1C=CC=CC=1.[CH2:36]([O:38][C:39](=[O:59])[C:40]([C:42]1[O:46][C:45]([C:47]2[CH:52]=[CH:51][C:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:49][CH:48]=2)=[CH:44][CH:43]=1)=[O:41])[CH3:37].[BH4-].[Na+]>>[CH2:36]([O:38][C:39](=[O:59])[CH:40]([C:42]1[O:46][C:45]([C:47]2[CH:52]=[CH:51][C:50]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)=[CH:49][CH:48]=2)=[CH:44][CH:43]=1)[OH:41])[CH3:37]Participants
4
Reactant 3
Product 1
Procedure
According to the procedure described in Example 13 for the preparation of 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-2-hydroxy-ethanone, 2-(2-biphenyl-4-yl-furan-5-yl)-2-oxoacetic acid ethyl ester was reduced with NaBH4 to give in quantitative yield 2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester as a yellow solid, mp 75-80° C. (d), which was used crude without purification. 1H NMR: δ 7.73 (d, 2H, J=8.5 Hz), 7.62 (d, 4H, J=8.1 Hz), 7.45 (t, 2H, J=7.4 Hz), 7.35 (t, 1H, J=7.4 Hz), 6.66 (d, 1H, J=3.3 Hz), 6.48 (d, 1H, J=3.3 Hz), 5.24 (d, 1H, J=5.9 Hz), 4.36-4.28 (m, 2H), 3.42 (d, 1H, J=6.3 Hz), 1.30 (t, 3H, J=7.2 Hz).
Sources & evidence
- ORD record
- ord-328d210593e94948b3d8c85f9b62d842
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495699B2
Reaction notes
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