Sodium borohydride → [(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

HRID 1348610Notes

Reaction equation

HRID 1348610 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]=[O:18])[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(OC(=O)C)C.CCCCCCC>O1CCCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][OH:18])[C:12]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:11]=2[O:10][C@@H:9]1[CH3:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21899848Ethylacetate heptaneHCID 86605287[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester

Product 1

HCID 67077122[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl esterYield 60.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.10 g (0.28 mmol) [(6R,7S)-2-Fluoro-6-methyl-8-oxo-9-(2-oxo-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester in 4 ml tetrahydrofurane were reduced with 0.02 g (0.34 mmol) sodium borohydride. Chromatography on silicagel with ethylacetate/heptane 8:2 yielded 0.06 g (56%) [(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-carbamic acid tert-butyl ester, MS m/e (%): 377.3 (M+Na+, 86), 355.2 (M+H+, 14), 255.3 (100).

Sources & evidence

ORD record
ord-a6b72a43e1eb458cb8f27b9dae83daea
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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