Aluminium lithium hydride → HCID 23627270, compound

HRID 1171901Notes

Reaction equation

[CH2:1]([C@H:8]1[NH:13][C:12](=O)[CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([C@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(R)-6-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-2-one (Compound 53) (365 mg, 0.959 mmol) was dissolved in THF (10 mL), cooled to 0° C., and treated with solid lithium aluminum hydride (73 mg, 1.92 mmol). The reaction mixture was heated at 60° C. for 3 hr then cooled to 0° C. and quenched with EtOAc (2 mL) and a 1 N aqueous solution of NaOH (2 mL). The reaction was filtered with the aid of EtOAc, dried over MgSO4, filtered, and evaporated to an oil, which was purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant to afford product as a brown colored oil (228 mg, 65%). LC/MS 5.12 min, [M+1]+ 367.

Workup

temperatureThe reaction mixture was heated at 60° C. for 3 hr
temperaturethen cooled to 0° C.
customquenched with EtOAc (2 mL)
filtrationThe reaction was filtered with the aid of EtOAc
dry with materialdried over MgSO4
filtrationfiltered
customevaporated to an oil, which
customwas purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant

Sources & evidence

ORD record: ord-cf86746e556745bcb9c37c83787e344c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829713B2

Reaction notes

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