Water → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(hydroxymethyl)pyrrolidine

HRID 1377759Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20](OC)=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([CH2:20][OH:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (500 mg, 1.57 mmol) in 7 mL of THF at 0° C. was added LiAlH4 (60 mg, 1.57 mmol). The resulting mixture was stirred for 15 min at 0° C. and then allowed to stir at room temperature for 20 min. The mixture was then successively treated dropwise with H2O (0.06 mL), 15% NaOH (0.06 mL), and H2O (0.18 mL). The resulting suspension was then stirred for 1 hr, filtered through Celite, and concentrated under reduced pressure to an oil. Silica gel chromatography (1:1 CHCl3 :methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(hydroxymethyl)pyrrolidine as a pale yellow oil (329 mg, 72%). 1H-NMR (300 MHz): δ 2.35 (m, 1), 2.90-3.08 (m, 3), 3.30-3.76 (m, 4), 3.82 (s, 3).

Workup

stirringto stir at room temperature for 20 min
stirringThe resulting suspension was then stirred for 1 hr
filtrationfiltered through Celite
concentrationconcentrated under reduced pressure to an oil

Sources & evidence

ORD record: ord-c8e57764cd184148936b3b0a4897d612
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665754

Reaction notes

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