Sodium borohydride → 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-ethanone

HRID 2299997Notes

Reaction equation

HRID 2299997 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]([C@H:43]1[CH2:47][O:46][C:45]([CH3:49])([CH3:48])[N:44]1[C:50](=[O:70])[C:51]([C:53]1[O:57][C:56]([C:58]2[CH:63]=[CH:62][C:61]([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[CH:60][CH:59]=2)=[CH:55][CH:54]=1)=[O:52])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[BH4-].[Na+]>>[CH2:36]([C@H:43]1[CH2:47][O:46][C:45]([CH3:49])([CH3:48])[N:44]1[C:50](=[O:70])[CH:51]([C:53]1[O:57][C:56]([C:58]2[CH:59]=[CH:60][C:61]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)=[CH:62][CH:63]=2)=[CH:55][CH:54]=1)[OH:52])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 183412571-(4(S)-benzyl-2, 2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-2-hydroxy-ethanoneHCID 183412611-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(2-biphenyl-4-yl-furan-5-yl)ethane-1, 2-dione

Product 1

HCID 183412601-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-ethanone

Procedure

According to the procdure 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, 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(2-biphenyl-4-yl-furan-5-yl)ethane-1,2-dione was reduced with NaBH4 to give in quantitative yield 1-(4(S)-benzyl-2,2-dimethyl-oxazolidin-3-yl)-2-(2-biphenyl-4-yl-furan-5-yl)-2-hydroxy-ethanone. 1H NMR: δ 7.70 (d, 2H, J=7.7 Hz), 7.61 (d, 4H, J=8.5 Hz), 7.45 (t, 2H, J=7.4 Hz), 7.38-7.19 (m, 6H), 6.64 (d, 1H, J=2.9 Hz), 6.43 (d, 1H, J=3.3 Hz), 5.08 (d, 1H, J=6.6 Hz), 4.45 (d, 1H, J=7.0 Hz), 3.88-3.85 (m, 1H), 3.78 (d, 1H, J=8.8 Hz), 3.63 (dd, 1H, J=5.2, 8.8 Hz), 3.03 (dd, 1H, J=4.2, 13.1 Hz), 2.89 (dd, 1H, J=9.8, 13.4 Hz), 1.83 (s, 3H), 1.58 (s, 3H). Anal. Calculated for C30H29NO4.0.5 H2O: C, 75.61; H, 6.34; N, 2.94. Found: C, 75.62; H, 6.32; N, 2.88.

Sources & evidence

ORD record
ord-c40b30c2ac4d473aa8457d7d7ad2c995
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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