HCID 69621453, compound → HCID 9838075, compound

HRID 1830966Notes

Reaction equation

HRID 1830966 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 acetate (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) δ2.08 (m, 2H); 2.29 (m, 2H); 3.53-3.63 (m, 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) δ24.2; 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-c6559abc4d1c4574bb7a0c2df9e02a87
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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