HCID 1214544, compound → (R)-(-)-2-(Anilinomethyl)pyrrolidine

HRID 2186476Notes

Reaction equation

[NH:1]1[CH2:14][CH2:13][CH2:12][C@@H:2]1[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH:5]([CH2:3][C@H:2]1[CH2:12][CH2:13][CH2:14][NH:1]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of D-Proline anilide (1.15 g, 6.0 mmol) in 20 mL of THF at 0° C. was added a 1 M solution of lithium aluminum hydride (14 mL, 14 mmol) in THF. The resulting solution was stirred at 0° C. for 11 hours. The reaction was carefully quenched with a saturated solution of Na2SO4 and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound as an oil. The oil was purified by silica gel chromatography with 3% CH3OH/CH2Cl2 and 1% triethyl amine to give the title compound as a yellow oil (0.029 g, 63%). ES (+) MS m/e=177 (M+H)

Workup

customThe reaction was carefully quenched with a saturated solution of Na2SO4
extractionextracted with EtOAc
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-514b749c9e7a476c83721ac09e158c64
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403792B1

Reaction notes

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