Ethyl formate → 9-(5-Chloro-thiophene-2-sulfonyl)-2-hydroxymethylene-9-aza-bicyclo[3.3.1]nonan-3-one
Reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH:15]3[CH2:16][CH2:17][CH2:18][CH:11]2[CH2:12][C:13](=[O:19])[CH2:14]3)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH:20](OCC)=[O:21].[O-]CC.[Na+]>C1COCC1.C(O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]2[CH:11]3[CH2:18][CH2:17][CH2:16][CH:15]2[C:14](=[CH:20][OH:21])[C:13](=[O:19])[CH2:12]3)(=[O:8])=[O:9])=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a stirring mixture of 9-(5-chloro-thiophene-2-sulfonyl)-9-aza-bicyclo[3.3.1]nonan-3-one (160 mg, 0.50 mmol) in THF/ethanol (3 mL, 1/1, v/v) was added ethyl formate (500 mg, 6.76 mmol) followed by sodium ethoxide (0.56 mL of 21% solution in ethanol). The resulting mixture was heated to 60° C. for 30 minutes after which the solution was cooled to room temperature and quenched by the addition of a saturated aqueous NH4Cl solution (10 mL). The resulting mixture was extracted with EtOAc (2×20 mL) and the combined organic phases were dried (Na2SO4), filtered and concentrated under vacuum to yield 9-(5-chloro-thiophene-2-sulfonyl)-2-hydroxymethylene-9-aza-bicyclo[3.3.1]nonan-3-one as a white solid. This crude product was directly taken to the next reaction without any further purification. Retention time (min)=1.985 min, Method [1], MS (ESI) 348.0 (M+H).
Workup
- temperaturewas cooled to room temperature
- customquenched by the addition of a saturated aqueous NH4Cl solution (10 mL)
- extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
- dry with materialthe combined organic phases were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-8f1ce0dd05644ebe98faa9ce5e6e5817
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345056B2
Reaction notes
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