Aluminium lithium hydride → HCID 68704566, compound

HRID 1972260Notes

Reaction equation

[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)[C:15]#[N:16])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)=[CH:31][CH:32]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A suspension of the α-amino nitrile (3 g, 6.8 mmol) from Step 1 in ether is cooled to −78° C. and is treated with lithium aluminum hydride (1.0 M solution in ether, 27.2 mmol) via slow addition. The cooling bath is removed and the reaction is allowed to warm to room temperature. Upon completion, 500 μL of water is added at 0° C. and the mixture stirred for 15 min. The mixture is filtered through a bed of Celite and the filtrate concentrated and purified by silica gel chromatography (eluting with 7N NH3 in IPA/methanol/dichloromethane 0.1:1:9) to give 1.5 g of 4-(4-chlorophenoxy)-N-(2-amino-1-(3-(benzyloxy)phenyl)ethyl)benzenamine as an oily brownish foam (50%).

Workup

customThe cooling bath is removed
temperatureto warm to room temperature
additionUpon completion, 500 μL of water is added at 0° C.
filtrationThe mixture is filtered through a bed of Celite
concentrationthe filtrate concentrated
custompurified by silica gel chromatography (eluting with 7N NH3 in IPA/methanol/dichloromethane 0.1:1:9)

Sources & evidence

ORD record: ord-3e760f688d3b40d98ea3c2d0925d8e3f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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