Aluminium lithium hydride → 3-Amino-1-(5-(cyclohexylethynyl)furan-2-yl)propan-1-ol

HRID 63323Notes

Reaction equation

HRID 63323 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:13]#[C:14][C:15]2[O:19][C:18]([C:20](=[O:24])[CH2:21][C:22]#[N:23])=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[NH2:23][CH2:22][CH2:21][CH:20]([C:18]1[O:19][C:15]([C:14]#[C:13][CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:16][CH:17]=1)[OH:24]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86694618HCID 86694618, compound

Product 1

HCID 866946173-Amino-1-(5-(cyclohexylethynyl)furan-2-yl)propan-1-ol

Procedure

LiAlH4 reduction of 3-(5-(cyclohexylethynyl)furan-2-yl)-3-oxopropanenitrile following the method used in Example 1 gave after flash chromatography purification (2%-20% 7N NH3/MeOH—CH2Cl2 gradient) followed by treatment with activated charcoal Example 23 as a light yellow oil. Yield (0.14 g, 26%); 1H NMR (400 MHz, CD3OD) δ 6.39 (d, J=3.4 Hz, 1H), 6.24 (d, J=3.9 Hz, 1H), 4.68 (t, J=6.8 Hz, 1H), 2.69-2.79 (m, 2H), 2.56-2.64 (m, 1H), 1.90-1.98 (m, 2H), 1.81-1.90 (m, 2H), 1.68-1.80 (m, 2H), 1.28-1.68 (m, 6H); RP-HPLC tR=9.95 min; ESI-MS m/z 230.2 [M−H2O+H]+.

Workup

  1. customgave
  2. customafter flash chromatography purification (2%-20% 7N NH3/MeOH—CH2Cl2 gradient)
  3. customYield (0.14 g, 26%)

Sources & evidence

ORD record
ord-61d8e2b49af74101bb2e3a007065f1ff
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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