Allyl bromide → ((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester

HRID 1348608Notes

Reaction equation

HRID 1348608 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:24])[NH:9][C@@H:10]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:13]=2[O:12][C@@H:11]1[CH3:23])([CH3:6])([CH3:5])[CH3:4].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C)C=O>[C:3]([O:7][C:8](=[O:24])[NH:9][C@@H:10]1[C:16](=[O:17])[N:15]([CH2:27][CH:26]=[CH2:25])[C:14]2[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:13]=2[O:12][C@@H:11]1[CH3:23])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67076781(6R,7S)-7-(Boc-amino)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten

Product 1

HCID 67076945((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.28 g (6.44 mmol) sodium hydride in 40 ml dimethylformamide were added at 0° C. 2.0 g (6.44 mmol) ((6R,7S)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester in 20 ml dimethylformamide. After 30 minutes 0.55 ml (6.44 mmol) allyl bromide was added. Stirring was continued for 3 hours. Extraction with ethylacetate/water and chromatography on silicagel with heptane to ethylacetate/heptane 1:1 yielded 2.24 g (99%) ((6R,7S)-9-allyl-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid tert-butyl ester, MS m/e (%): 351.2 (M+H+, 80), 295.3 (100), 251.1 (82).

Workup

  1. additionwere added at 0° C
  2. extractionExtraction with ethylacetate/water and chromatography on silicagel with heptane to ethylacetate/heptane 1:1

Sources & evidence

ORD record
ord-2f97cf609b7b4794bfc46773e9f747be
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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