Sodium borohydride → 2-(2-Biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester

HRID 382204Notes

Reaction equation

HRID 382204 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

HCID 4311764Sodium borohydrideHCID 183412571-(4(S)-benzyl-2, 2-dimethyl-oxazolidin-3-yl)-2-(biphenyl-4-yl-1H-pyrrol-3-yl)-2-hydroxy-ethanoneHCID 183415122-(2-Biphenyl-4-yl-furan-5-yl)-2-oxoacetic acid ethyl ester

Product 1

HCID 183415112-(2-Biphenyl-4-yl-furan-5-yl)-2-hydroxy-acetic acid ethyl ester

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.

Sources & evidence

ORD record
ord-48ddb6691f8549bfbbade74094633c04
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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