Tetrahydrofuran → HCID 69432639, compound

HRID 1270004Notes

Reaction equation

HRID 1270004 reaction equation
[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][CH2:19][C:20](OCC)=[O:21])[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][CH2:19][CH2:20][OH:21])[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69431098HCID 69431098, compound

Product 1

HCID 69432639HCID 69432639, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The ethyl N-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}glycinate obtained in Example 836 was added to a tetrahydrofuran suspension of lithium aluminum hydride, and the resulting mixture was stirred at room temperature for 3 hours. Water, a 2N-aqueous sodium hydroxide solution and then water were added to the reaction mixture and stirred for 1 hour, followed by filtration using Celite. The filtrate was concentrated and then purified by a preparative thin-layer chromatography (methanol (containing aqueous ammonia)/chloroform=1/10) to obtain 2-({cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}amino)ethanol (17.6 mg, 40%).

Workup

  1. stirringstirred for 1 hour
  2. filtrationfollowed by filtration
  3. concentrationThe filtrate was concentrated
  4. custompurified by a preparative thin-layer chromatography (methanol (containing aqueous ammonia)/chloroform=1/10)

Sources & evidence

ORD record
ord-ecf4ca380d8845678c2198bdbd6f04ca
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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