Toluene → HCID 69155296, compound

HRID 1294623Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@@H:11]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19](OC)=[C:18]([O:24][CH3:25])[CH:17]=3)[NH:12]2)=O)=[CH:4][C:3]=1[O:26][CH3:27].C1(C)C=CC=CC=1.C1C[O:38][CH2:37]C1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C@@H:11]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH2:17][C:18]([O:24][CH3:25])([O:38][CH3:37])[CH:19]=[CH:20][CH:21]=3)[NH:12]2)=[CH:4][C:3]=1[O:26][CH3:27]

Participants

Reactant 3

HCID 1140Toluene

HCID 8028Tetrahydrofuran

HCID 86597236HCID 86597236, compound

Product 1

HCID 69155296HCID 69155296, compoundYield 67%

Conditions

Temperature: 0 °C

Procedure

(2S,5R)5-(3,4-Dimethoxy-phenyl)-pyrrolidine-2-carboxylic acid (4-chloro-3-methoxy-phenyl)-amide was dissolved in anhydrous THF and cooled to 0° C. in an ice bath. A 0.5M solution of alane complex in toluene (42.6 ml, 21.3 mmol, 3.0 equivalents) was added slowly and the reaction was allowed to stir and warn to room temperature overnight. The reaction was quenched upon addition of ethyl acetate:methanol (1:1, 5 ml). The resulting slurry was filtered through Celite and rinsed with ethyl acetate. The filtrate was concentrated in vacuo to afford (2S,5R)(4-chloro-3-methoxy-phenyl)-[5-(3,3-dimethoxy-phenyl)-pyrrolidin-2-ylmethyl]-amine (1.80 g, 4.78 mmol, 67% yield). Analysis H1 NMR (400 MHz, CDCl3): 7.12 (1H, d), 6.98–6.90 (3H, m), 6.23 (1H, s), 6.19 (1H, d) 4.39-4.15 (2H, m), 3.76-3.53 (1H, m), 3.30–2.97 (2H, m), 2.34–1.55 (6H, m). MS (LC-MS): Calculated for C20H25ClN2O3 376.16. Found 377.21 (M+H)+.

Workup

customThe reaction was quenched upon addition of ethyl acetate:methanol (1:1, 5 ml)
filtrationThe resulting slurry was filtered through Celite
washrinsed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-661c64900e3043b1aab3610cb844b916
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241765B2

Reaction notes

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