Aluminium lithium hydride → 2-(3-(1-Admantyl)-4-isopropoxyphenyl)ethanamine

HRID 710450Notes

Reaction equation

HRID 710450 reaction equation
[C:1]12([C:11]3[CH:16]=[C:15](/[CH:17]=[CH:18]/[N+:19]([O-])=O)[CH:14]=[CH:13][C:12]=3[O:22][CH:23]([CH3:25])[CH3:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]12([C:11]3[CH:16]=[C:15]([CH2:17][CH2:18][NH2:19])[CH:14]=[CH:13][C:12]=3[O:22][CH:23]([CH3:24])[CH3:25])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66727011(E)-2-(1-Admantyl)-1-isopropoxy-4-(2-nitrovinyl)benzene

Product 1

HCID 667263922-(3-(1-Admantyl)-4-isopropoxyphenyl)ethanamineYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the product of Step B (0.27 g, 0.8 mmol) in anhydrous Et2O (10 ml) was added drop wise to the stirred slurry of LiAlH4 (0.040 g) in anhydrous Et2O (5 ml). After addition the mixture was stirred for 1 h at room temperature and then quenched with a mixture of Et2O:EtOAc:MeOH:H2O; 80:15:4:1. The white solid was separated and filtered through Celite bead. The filtrate was evaporated to dryness to give the title compound (0.235 g; 96%). 1H-NMR CDCl3) 1.35 (d, 6H, J=5.9 Hz); 1.59 (s, 6H); 1.7 (s, 9H); 1.73 (s, 6H); 2.03-2.12 (m, 9H); 2.69 (m, 2H); 2.93 (m, 2H); 4.55-4.6 (m, 1H); 6.72 (d, 1H, J=8.46 Hz); 6.9-6.99 (m, 2H).

Workup

  1. additionAfter addition the mixture
  2. customquenched with a mixture of Et2O
  3. customThe white solid was separated
  4. filtrationfiltered through Celite bead
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-b447cdbedcba4945b53c8e499e2f7ea7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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