Triethylamine → HCID 58486364, compound
Reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][C@H:11]([CH3:13])[O:10][C@H:9]([CH3:14])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:27])[C:22]([CH3:24])([CH3:23])[O:21][B:20]([CH:25]=[CH2:26])[O:19]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:14][C@H:9]1[O:10][C@@H:11]([CH3:13])[CH2:12][N:7]([CH2:6][C:5]2[CH:15]=[CH:16][C:2](/[CH:26]=[CH:25]/[B:20]3[O:21][C:22]([CH3:24])([CH3:23])[C:18]([CH3:27])([CH3:17])[O:19]3)=[CH:3][CH:4]=2)[CH2:8]1Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-(4-bromobenzyl)-cis-2,6-dimethylmorpholine (20 g, 71 mmol) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (13 mL, 77 mmol, 1.1 eq.) in toluene (250 mL) was added triethylamine (19.7 mL, 142 mmol) and Pd(PtBu3)2 (368 mg, 0.71 mmol) and the solution was heated to 80° C. for 2 h under argon. After cooling to rt, the reaction was quenched with sat. NaHCO3 (50 mL), water (50 mL), extracted with EtOAc (3×100 mL) and dried over MgSO4. After evaporation of the solvents, the residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%) to give the title compound as a white solid (16 g, 64%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, J=8.0 Hz, 2H), 7.40 (d, J=18.4 Hz, 1H), 7.30 (d, J=7.6 Hz, 2H), 6.16 (d, J=18.4 Hz, 1H), 3.75-3.65 (m, 2H), 3.47 (s, 2H), 2.70 (d, J=10.8 Hz, 2H), 1.75 (t, J=10.2 Hz, 2H), 1.32 (s, 12H), 1.14 (d, J=6.4 Hz, 6H); MS ESI 358.2 [M+H]+, calcd for [C21H32BNO3+H]+ 358.2.
Workup
- temperatureAfter cooling to rt
- customthe reaction was quenched with sat. NaHCO3 (50 mL), water (50 mL)
- extractionextracted with EtOAc (3×100 mL)
- dry with materialdried over MgSO4
- customAfter evaporation of the solvents
- customthe residue was purified by Biotage column system (EtOAc/hex gradient: 0-100%)
Sources & evidence
- ORD record
- ord-30fbc7f8485746a7a642316df16a6403
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921545B2
Reaction notes
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