1,2-Dichloroethane → HCID 57744213, compound
Reaction equation
[OH:1][CH2:2][C@H:3]1[NH:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[C:16](O)(=O)[CH3:17].C(O[BH-](O[C:30](=O)[CH3:31])OC(=O)C)(=O)C.[Na+].[C:34](=O)(O)[O-].[Na+].Cl[CH2:40][CH2:41]Cl>>[CH2:34]([N:8]1[CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C@H:3]1[CH2:2][OH:1])[C:16]1[CH:17]=[CH:31][CH:30]=[CH:41][CH:40]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a 250 mL round bottom flask was added 15L (10.93 g, 50.5 mmol) and 1,2-dichloroethane (144 mL). Acetic acid (3.03 g, 1 eq) was added and the flask was cooled to 0° C. Sodium triacetoxyborohydride (13.91 g, 1.3 eq) was slowly added. The flask was warmed to room temperature and stirred overnight at room temperature. The reaction mixture was poured onto saturated sodium bicarbonate. The organic layer was separated and the aqueous was extracted two times with ethyl acetate. The organic were combined and washed once with brine. The organics were dried over sodium sulfate and filtered. Solvent was removed under vacuum. The residue was purified by column chromatography with 50% ethyl acetate in hexanes to give a white solid 15N (13.07 g, 84%).
Workup
- temperatureThe flask was warmed to room temperature
- customThe organic layer was separated
- extractionthe aqueous was extracted two times with ethyl acetate
- washwashed once with brine
- dry with materialThe organics were dried over sodium sulfate
- filtrationfiltered
- customSolvent was removed under vacuum
- customThe residue was purified by column chromatography with 50% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-0ab41b2f42ef4d139020bc38113728dd
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08148367B2
Reaction notes
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