Triethylamine → (1R)-2-[1-(3-Ethoxy-4-methoxy-phenyl)-3-hydroxy-propyl]-7-nitro-2,3-dihydro-isoindol-1-one

HRID 658145Notes

Reaction equation

HRID 658145 reaction equation
[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH2:15][CH3:16])[CH:7]=1)[CH2:3][CH2:4][OH:5].C[O:18][C:19](=O)[C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:29]Br.C(N(CC)CC)C>CN(C=O)C>[CH2:15]([O:14][C:8]1[CH:7]=[C:6]([C@H:2]([N:1]2[CH2:29][C:21]3[C:20](=[C:25]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:23][CH:22]=3)[C:19]2=[O:18])[CH2:3][CH2:4][OH:5])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21708527Methyl 2-(bromomethyl)-6-nitrobenzoateHCID 67175570(3R)-3-amino-3-(3-ethoxy-4-methoxyphenyl)propan-1-ol

Product 1

HCID 67175146(1R)-2-[1-(3-Ethoxy-4-methoxy-phenyl)-3-hydroxy-propyl]-7-nitro-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1R)-2-[1-(3-Ethoxy-4-methoxy-phenyl)-3-hydroxy-propyl]-7-nitro-2,3-dihydro-isoindol-1-one was prepared by the procedure of Example 1 from (3R)-3-amino-3-(3-ethoxy-4-methoxy-phenyl)-propan-1-ol (3.0 g, 13 mmol), 2-bromomethyl-6-nitro-benzoic acid methyl ester (3.6 g, 13 mmol) and triethylamine (2 mL, 14 mmol) in DMF (40 mL) to give a yellow solid (4.1 g, 81% yield): 1H NMR (CDCl3) δ 1.44 (t, J=7 Hz, 3H, CH3), 2.13-2.31 (m, 2H, CH2), 3.54-3.59 (m, 1H, CHH), 3.71-3.77 (m, 1H, NCHH), 3.87 (s, 3H, CH3), 3.94 (d, J=16 Hz, 1H, NCHH), 4.06 (q, J=7 Hz, 2H, CH2), 4.26 (d, J=16 Hz, 1H, NCHH), 5.70 (dd, J=4, 11 Hz, 1H, NCH), 6.85-6.99 (m, 3H, Ar), 7.55-7.77 (m, 3H, Ar); 13C NMR (CDCl3) δ 14.76, 33.92, 45.80, 51.30, 55.98, 58.65, 64.63, 65.84, 111.39, 113.22, 119.75, 122.91, 124.13, 126.74, 130.66, 132.11, 143.84, 146.66, 148.68, 149.33, 164.22.

Sources & evidence

ORD record
ord-74fbbcb9943743fbaa93e29bc637fffa
Source dataset
uspto-grants-2011_12
Patent number
US08076369B2

Reaction notes

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