Water → HCID 18399718, compound

HRID 1019003Notes

Reaction equation

HRID 1019003 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]2[N:25]=[CH:26][CH:27]=[C:28]3[CH:32]=[CH:31][O:30][C:29]=23)[CH2:20][CH2:19]1)[C:13](=O)OCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[O:30]1[C:29]2=[C:24]([N:21]3[CH2:20][CH2:19][CH:18]([N:12]([CH3:13])[CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH2:23][CH2:22]3)[N:25]=[CH:26][CH:27]=[C:28]2[CH:32]=[CH:31]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18399766HCID 18399766, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18399718HCID 18399718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 700 mg of the product obtained in Step A in 20 ml of tetrahydrofuran is added at 0° C. to a suspension of 123 mg of LiAlH4 in 20 ml of tetrahydrofuran. The whole is stirred for 3 hours at ambient temperature and then hydrolysed with 0.17 ml of water, 0.5 ml of 20% sodium hydroxide solution and 0.70 ml of water. The whole is filtered, evaporated and purified by chromatography on silica gel (dichloromethane/ethanol: 95/5), enabling the expected product to be isolated.

Workup

  1. filtrationThe whole is filtered
  2. customevaporated
  3. custompurified by chromatography on silica gel (dichloromethane/ethanol: 95/5)
  4. customto be isolated

Sources & evidence

ORD record
ord-f140d408334c4aeabec3da1c2ca2a96b
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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