Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-(4-(2-(6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy)benzyl) azetidine-3-carboxylic acid

HRID 2046090Notes

Reaction equation

HRID 2046090 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH:19]3[CH2:24][CH2:23][CH:22]4[CH2:25][CH:20]3[C:21]4([CH3:27])[CH3:26])=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[CH3:26][C:21]1([CH3:27])[CH:20]2[CH2:25][CH:22]1[CH2:23][CH2:24][CH:19]2[CH2:18][CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:7]2[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 66615020Methyl-1-(4-(2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy)benzyl)azetidine-3-carboxylate

Product 1

HCID 462002971-(4-(2-(6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy)benzyl) azetidine-3-carboxylic acidYield 87%

Procedure

When the product of Step B was substituted for methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate in Example 25, Step E, the similar procedure afforded the title compound in 87% yield, as creamy paste. 1H-NMR (CDCl3+CD3OD) 7.21 (d, 2H, J=7.98 Hz); 6.79 (d, 2H, J=7.99 Hz); 3.94-3.71 (m, 8H); 3.27-3.25 (m, 1H); 2.36-1.20 (m, 10H); 1.14 (s, 3H); 0.97 (s, 3H).

Sources & evidence

ORD record
ord-74f548efc1df479d98fdba01ee45c05a
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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