Water → HCID 59457500, compound

HRID 1710804Notes

Reaction equation

[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][N:23]3[C@H:27]([CH2:28][N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[CH2:26][CH2:25][C:24]3=O)[N:21]=2)=[CH:13][CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][C@H:27]3[CH2:28][N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[N:21]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(5S)-1-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]-5-(morpholin-4-ylmethyl)pyrrolidin-2-one 137 (0.21 g, 1 eq, 0.43 mmol) is dissolved in tetrahydrofuran (5 ml), then the mixture is cooled to 0° C. and lithium aluminium hydride (0.03 g, 2 eq, 0.87 mmol) is added. The mixture is stirred 1 h at 0° C. and then overnight at room temperature. Water (0.05 ml), a solution of sodium hydroxide 2N (0.05 ml) and again water (0.15 ml) are added. Then, the mixture is filtered through celite and concentrated under vacuum. Purification by chromatography on silicagel (eluent: dichloromethane/methanol/ammonia 951510.5) affords 0.058 g of 4-({(2S)-1-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]pyrrolidin-2-yl}methyl)morpholine 144.

Workup

customovernight
customat room temperature
filtrationThen, the mixture is filtered through celite
concentrationconcentrated under vacuum
customPurification by chromatography on silicagel (eluent: dichloromethane/methanol/ammonia 951510.5)

Sources & evidence

ORD record: ord-330eaf37e4d54395bac38737bfec8005
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790720B2

Reaction notes

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