Ethyl Acetate → HCID 86718379, compound
Reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C@@H:7]([CH3:23])[C@H:8]([N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)C.[BH4-].[Li+].CCOC(C)=O>C1COCC1>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C@@H:8]([N:14]([CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C@H:7]([CH3:23])[CH2:6][CH2:5][CH2:4][OH:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of compound 2.12d (0.6 g, 1.77 mmol) in THF (3.5 mL) was added lithium borohydride (2.0 M in THF, 8.8 mL, 17.7 mmol, 10.0 equiv) and the resulting mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled at room temperature and EtOAc (2.0 mL) was added. After stirring for 10 minutes, the reaction mixture was quenched by addition of 1.0 N HCl aqueous solution. The phases were separated and the aqueous layer was extracted with DCM. The organic layer was dried over sodium sulfate, filtered and concentrated to give product 2.19.1a (0.54 g) which was used in the next step with no further purification. MS m/z (M+Na) 320.2
Workup
- temperatureThe reaction mixture was cooled at room temperature
- stirringAfter stirring for 10 minutes
- customthe reaction mixture was quenched by addition of 1.0 N HCl aqueous solution
- customThe phases were separated
- extractionthe aqueous layer was extracted with DCM
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give product 2.19.1a (0.54 g) which
- customwas used in the next step with no further purification
Sources & evidence
- ORD record
- ord-dfb2e5f29e084d0a9e5196f2013afee8
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09072696B2
Reaction notes
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