Hydrochloric Acid → Ethyl 2-allyl-2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate
Reaction equation
[CH2:1]([C:4]([N:23]=C(C1C=CC=CC=1)C1C=CC=CC=1)([CH2:10][CH2:11][CH2:12][CH2:13][B:14]1[O:18][C:17]([CH3:20])([CH3:19])[C:16]([CH3:22])([CH3:21])[O:15]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3].Cl>C(OCC)C>[CH2:1]([C:4]([NH2:23])([CH2:10][CH2:11][CH2:12][CH2:13][B:14]1[O:15][C:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[O:18]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 2-allyl-2-(diphenylmethyleneamino)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (0.32 g, 0.65 mmol) in diethyl ether (3.4 mL, 0.2 M) was treated with 1N HCl (3 mL). After stirring 16 h, the layers were separated and the aqueous phase was diluted with saturated aqueous K2CO3 and extracted with chloroform to give ethyl 2-allyl-2-amino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate as a colorless oil (0.20 g, 94%). Rf 0.62 (10% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 5.76-5.60 (m, 1H), 5.18-5.07 (m, 2H), 4.15 (q, J=7.2 Hz, 2H), 2.54 (ddt, J1=13.5 Hz, J2=6.3 Hz, J3=1.2 Hz, 1H), 2.23 (dd, J1=13.5 Hz, J2=8.7 Hz, 1H), 1.8-1.68 (m, 2H), 1.70-1.60 (m, 1H), 1.60-1.46 (m, 2H), 1.46-1.32 (m, 3H), 1.24 (s, 12H), 1.20-1.06 (m, 1H), 0.766 (t, J=7.8 Hz, 2H); ESI-LCMS m/z calcd for C17H32BNO4: 325.2. found 326.2 (M+H)+.
Workup
- customthe layers were separated
- additionthe aqueous phase was diluted with saturated aqueous K2CO3
- extractionextracted with chloroform
Sources & evidence
- ORD record
- ord-70d08aeeb8ce43b3bd8b420d624047a2
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040703B2
Reaction notes
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