Toluene → HCID 69155296, compound
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
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 warm 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
- temperaturewarm to room temperature overnight
- 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-be5af26909e14ae8ae732c45c2af424c
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07081458B2
Reaction notes
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