Pyrrolidine → 1-(4-(Azetidin-3-yloxy)-2-methoxy-3-methylbenzyl)pyrrolidine

HRID 1035215Notes

Reaction equation

HRID 1035215 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[O:5][CH:6]1[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1.N1C[CH:28]([O:30]C2C=CC(CN3CCCC3)=C(F)C=2)C1.N1CCC[CH2:45]1.OC1C=CC(C=O)=C(OC)C=1C>>[NH:8]1[CH2:7][CH:6]([O:5][C:4]2[CH:17]=[CH:18][C:19]([CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)=[C:2]([O:30][CH3:28])[C:3]=2[CH3:45])[CH2:9]1

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 58043122HCID 58043122, compoundHCID 58043143tert-Butyl 3-(3-fluoro-4-(pyrrolidin-1-ylmethyl)phenoxy)azetidine-1-carboxylateHCID 666533591-(4-(Azetidin-3-yloxy)-2-fluorobenzyl)pyrrolidine

Product 1

HCID 666559581-(4-(Azetidin-3-yloxy)-2-methoxy-3-methylbenzyl)pyrrolidineYield 30%

Procedure

Using similar protocols as described in Examples 31A, 31B and 31C employing pyrrolidine and 52A as starting materials afforded 0.25 g (30%) of 52B as an oil. 1H NMR (500 MHz, CDCl3): δ 1.75 (s, 4H), 2.16 (s, 3H), 2.51 (s, 4H), 3.70 (s, 2H), 3.74 (s, 3H), 3.79 (m, 2H), 3.91 (m, 2H), 4.97 (m, 1H), 6.29 (d, 1H), 7.11 (d, 1H), MS (APCI+) m/z 277 [M+H]+.

Sources & evidence

ORD record
ord-ecb74deaa72744f29f5d84a5cbee106d
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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