Methanol → (S,E)-tert-butyl 2-(4-(((4-aminobenzyl)(phenyl)amino)methyl)styryl)pyrrolidine-1-carboxylate

HRID 923448Notes

Reaction equation

[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][N:9]([CH2:16][C:17]2[CH:36]=[CH:35][C:20](/[CH:21]=[CH:22]/[C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Bi](Cl)(Cl)Cl.[BH4-].[Na+].CO>C(O)C>[NH2:1][C:4]1[CH:38]=[CH:37][C:7]([CH2:8][N:9]([CH2:16][C:17]2[CH:36]=[CH:35][C:20](/[CH:21]=[CH:22]/[C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product of Example 149E (0.8 g, 1.56 mmol) dissolved in ethanol (20 mL) was cooled in an ice bath to 0° C., then bismuth(III) chloride (1.47 g, 4.67 mmol) was added followed by the portionwise addition of sodium borohydride (943 mg, 24.92 mmol) and warming the solution to room temperature for 20 minutes. The methanol was added and the solid removed by filtration, the filtrate concentrated to an oil, which was redissolved with dichloromethane and extracted with aqueous sodium bicarbonate. The organic solution was then dried, filtered, and concentrated to afford the title compound. m/z 484 (M+H)+.

Workup

temperaturewarming the solution to room temperature for 20 minutes
customthe solid removed by filtration
concentrationthe filtrate concentrated to an oil, which
dissolutionwas redissolved with dichloromethane
extractionextracted with aqueous sodium bicarbonate
customThe organic solution was then dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-5eab25a08ced46e7975790ffc0cb89a5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

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