Methyl Acrylate → (+/-)-(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([NH:18][C:17](=[O:19])[C:16]3[CH:20]=[C:21](Br)[CH:22]=[CH:23][C:15]=3[O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27].COC(=O)/C=C/C1C=C2C(=CC=1)OC1(CNC1)CC2=O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:30][O:29][C:25](=[O:28])/[CH:26]=[CH:27]/[C:21]1[CH:22]=[CH:23][C:15]2[O:14][C:10]3([CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]3)[NH:18][C:17](=[O:19])[C:16]=2[CH:20]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of (±)-6-bromo-3,4-dihydro-4-oxo-spiro-[2H-(1,3)-benzoxazine-2,3′-piperidine]-1′-carboxylic acid tert-butyl ester (2.50 g, 6.30 mmol) in dry DMF (5 ml) was treated with Pd(OAc)2 (26.0 mg, 0.130 mmol), P(o-tol)3 (76.6 mg, 0.252 mmol), TEA (2.6 ml, 19 mmol) and methyl acrylate (1.7 ml, 19 mmol) following the procedure described for Intermediate 4, Step B, to give (±)-(E)-3-{1′-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester (2.30 g) as a light orange solid.
Sources & evidence
- ORD record
- ord-329b44228e5641ea9be145870d0ac10e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08980877B2
Reaction notes
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