Sodium borohydride → N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 1348649Notes

Reaction equation

HRID 1348649 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C@H:10]([CH3:12])[C@H:9]([N:13]([CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:14](=[O:21])[C:15]([OH:20])([CH3:19])[C:16]([NH2:18])=[O:17])[C:8](=[O:30])[N:7]([CH2:31][CH:32]=[O:33])[C:6]=2[CH:34]=1.[BH4-].[Na+].C(OC(=O)C)C.CCCCCCC>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C@H:10]([CH3:12])[C@H:9]([N:13]([CH2:22][C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[F:27])[C:14](=[O:21])[C:15]([OH:20])([CH3:19])[C:16]([NH2:18])=[O:17])[C:8](=[O:30])[N:7]([CH2:31][CH2:32][OH:33])[C:6]=2[CH:34]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21091481N-[(6R,7S)-2-Fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamideHCID 21899848Ethylacetate heptane

Product 1

HCID 86605289N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamideYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (2.0 mmol N-[(6R,7S)-2-Fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide in 30 ml tetrahydrofurane were reduced with 0.09 g (2.0 mmol) sodium borohydride. Chromatography on silicagel with ethylacetate/heptane 0:100 to 100:0 yielded 0.33 g (34%) N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide, MS m/e (%): 502.0 (M+H+, 100).

Sources & evidence

ORD record
ord-577755a38db84c95a35ef8fd42b068cc
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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