HCID 69621453, compound → HCID 9838075, compound

HRID 1826132Notes

Reaction equation

HRID 1826132 reaction equation
[CH2:1]([O:8][C:9]1[C:28]([O:29][CH3:30])=[CH:27][C:12]([C:13]([N:15]2[CH:19]=[C:18](CC(OC)=O)[CH2:17][C@H:16]2[CH2:25]O)=[O:14])=[C:11]([N+:31]([O-])=O)[CH:10]=1)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:30][O:29][C:28]1[C:9]([O:8][CH3:1])=[CH:10][C:11]2[N:31]=[CH:25][C@@H:16]3[CH2:17][CH2:18][CH2:19][N:15]3[C:13](=[O:14])[C:12]=2[CH:27]=1

Participants

3

Reactant 1

HCID 69621453HCID 69621453, compound2×

Product 1

HCID 9838075HCID 9838075, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Finely ground Cd/Pb couple (3.12 g) was added portion wise to a solution of 105 (1 g, 2.2 mmol) THF (10 mL) and NH4OAc (1M, 10 mL). The reaction was followed by TLC (EtOAc), when no starting material was present, the mixture was poured into ethyl aceate (400 mL). The organic phase was dried over MgSO4 and evaporated to yield the crude product, which was purified by flash chromatography (EtOAc) to give of the pure compound as a pale yellow oil (0.45 g, 78%) 1H NMR (270 MHz, CDCl3) δ 2.08 (m, 2H); 2.29 (m, 2H); 3.53-3.63 (n, 1H); 3.72 (m, 1H); 3.79-3.85 (m, 1H); 3.93 (s, 3H); 3.96 (s, 3H); 6.82 (s, 1H); 7.52 (s, 1H); 7.68 (d, J=4.4, 1H). 13C NMR (67.8 MHz, CDCl3) δ 24.2; 29.6; 46.7; 53.7; 56.0; 56.1; 109.4; 111.2; 140.7; 147.5; 151.3; 162.5; 164.6. IR (Nujol): cm−1 3000-2800, 1601, 1450, 1434, 1500, 1453, 1263, 1217, 1010, 908, 735. MS: m/e (relative intensity) 260 (M+, 100), 245 (50), 231 (25), 217 (10), 191 (20), 164 (25), 136 (20), 121 (5), 93 (8), 70 (10). HRMS Calculated for C14H16N2O3: 260.1160. Found: 260.1161. [α]25D=+1004.7° (c 0.17, CHCl3).

Sources & evidence

ORD record
ord-2338b784fe0e437c93d185769477dfe6
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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