Water → HCID 131722260, compound

HRID 565429Notes

Reaction equation

HRID 565429 reaction equation
[NH2:1][C:2]1([C:16]#[N:17])[CH2:15][CH2:14][C@H:13]2[C@@H:4]([CH2:5][C:6]3[C:11]([CH2:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:17][CH2:16][C:2]1([NH2:1])[CH2:15][CH2:14][C@H:13]2[C@@H:4]([CH2:5][C:6]3[C:11]([CH2:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10585357HCID 10585357, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131722260HCID 131722260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.39 g (6.1 mmol) of the nitrile obtained in Step 5 in 35 ml of THF is added dropwise to a suspension of LiAlH4 (350 mg, 9.2 mmol) in 35 ml of anhydrous THF at −20° C. under nitrogen. The mixture is stirred for 1 hour 30 before being hydrolysed with 2.3 ml of H2O, 4.6 ml of 35% sodium hydroxide solution and 4.9 ml of water. The resulting suspension is filtered and the filtrate is evaporated to yield an oil which is subjected to flash chromatography over a column: the title compound is isolated in the form of a mixture of two diastereoisomers which are separable by HPLC (Kromasil 100, 10 C18-210 mm—CH3CN/H2O/CF3COOH=170/830/5).

Workup

  1. filtrationThe resulting suspension is filtered
  2. customthe filtrate is evaporated
  3. customto yield an oil which

Sources & evidence

ORD record
ord-796061728b464aa1a449ea390522b63e
Source dataset
uspto-grants-2001_01
Patent number
US06172097B2

Reaction notes

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