Ethyl formate → HCID 67308098, compound

HRID 2061597Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH:18]([C:20]4[O:24][N:23]=[C:22]([CH3:25])[N:21]=4)[CH2:19][CH:12]2[CH2:13][C:14](=[O:26])[CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:27](OCC)=[O:28].[O-]CC.[Na+]>C1COCC1.CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:12]3[CH2:19][CH:18]([C:20]4[O:24][N:23]=[C:22]([CH3:25])[N:21]=4)[CH2:17][CH:16]2[C:15](=[CH:27][OH:28])[C:14](=[O:26])[CH2:13]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

9-[(4-Chlorophenyl)sulfonyl]-7-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-one (52) (0.357 g, 0.902 mmol) was dissolved in THF/EtOH (2 mL, 1/1, v/v). Ethyl formate (0.725 mL, 9.02 mmol) was added followed by sodium ethoxide (1.01 mL of 21% solution in EtOH). The resulting mixture was stirred at 50° C. for 1 hour after which the solution was cooled back to room temperature and quenched by the addition of saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc and the combined organic phases were dried (Na2SO4), filtered and concentrated under vacuum to give 9-[(4-chlorophenyl)sulfonyl]-2-(hydroxymethylidene)-7-(3-methyl-1,2,4-oxadiazol-5-yl)-9-azabicyclo[3.3.1]nonan-3-one (53). MS (ESI) 424.0 (M+H).

Workup

temperaturewas cooled back to room temperature
customquenched by the addition of saturated aqueous NH4Cl
extractionThe resulting mixture was extracted with EtOAc
dry with materialthe combined organic phases were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-aabf4150acea4d348e4090ebc08b7c5d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283358B2

Reaction notes

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