2,4-Difluorobenzaldehyde → HCID 59400138, compound
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:2]1.[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:21]=1[CH:22]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>ClCCCl>[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:21]=1[CH2:22][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:2]1Participants
5
Conditions
- Temperature
- 50 °C
Procedure
To a solution of tert-butyl 1,2,3,4-tetrahydroquinolin-3-ylcarbamate (248 mg, 1.0 mmol) and 2,4-difluorobenzaldehyde (300 mg, 2.11 mmol) in 1,2-dichloroethane (10 mL) was added tetramethylammonium triacetoxyborohydride (0.6 g, 2.0 mmol). The mixture was stirred at 50° C. for 20 hours. The mixture was quenched by addition of saturated Rochelle's salt (10 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by chromatography on silica gel (5-40% EtOAc/Hexane) to give tert-butyl 1-(2,4-difluorobenzyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (365 mg).
Workup
- customThe mixture was quenched by addition of saturated Rochelle's salt (10 mL)
- extractionextracted with dichloromethane (3×10 mL)
- washThe combined organic layers were washed with water (2×10 mL)
- dry with materialdried over anhydrous sodium sulfate
- customevaporated to dryness
- customThe residue was purified by chromatography on silica gel (5-40% EtOAc/Hexane)
Sources & evidence
- ORD record
- ord-c45f8df28ee245cfac8ffe1129365fe4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273754B2
Reaction notes
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