Isopropanol → HCID 17800145, compound

HRID 365502Notes

Reaction equation

HRID 365502 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[CH2:11][C:12]([CH3:24])([NH:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:13]#[N:14].[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(O)C.[Na+].[Cl-]>C1COCC1>[NH2:14][CH2:13][C:12]([NH:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])([CH2:11][C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH3:24]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5234Sodium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23292310HCID 23292310, compound

Product 1

HCID 17800145HCID 17800145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 16 g of the compound obtained in Step 1 in 200 ml of THF is added dropwise to a suspension, maintained under nitrogen, of 2.28 g (60 mmol) of LiAlH4 in 200 ml of THF. The temperature of the mixture is then increased to 20° C. and stirring is maintained at that temperature for 3 hours. The mixture is again cooled to 0° C. and hydrolysed by successive additions of 20 ml of iPrOH and 25 ml of saturated NaCl solution. The precipitate formed is suctioned off and rinsed with THF; the filtrate is concentrated in vacuo and the residue is chromatographed on silica, eluting with a mixture of CH2Cl2 /CH3OH/NH4OH=97/3/0.3, to yield the title compound in the form of 2 diastereoisomers:

Workup

  1. temperatureis maintained at that temperature for 3 hours
  2. customThe precipitate formed
  3. washrinsed with THF
  4. concentrationthe filtrate is concentrated in vacuo
  5. customthe residue is chromatographed on silica
  6. washeluting with a mixture of CH2Cl2 /CH3OH/NH4OH=97/3/0.3

Sources & evidence

ORD record
ord-cdf2b84ff8304e9bb310cb35c9567faa
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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