Aluminium lithium hydride → HCID 178520738, compound

HRID 1600681Notes

Reaction equation

HRID 1600681 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:14][CH2:13]1)C>C1COCC1>[N:20]1[CH:21]=[CH:22][CH:23]=[N:24][C:19]=1[NH:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([CH2:11][CH2:10][OH:9])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178471805HCID 178471805, compound

Product 1

HCID 178520738HCID 178520738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of lithium aluminum hydride (0.45 g, 11.85 mmol) is cooled in an ice water bath and treated with a solution of trans-[4-(pyrimidin-2-ylamino)-cyclohexyl]-acetic acid ethyl ester (2.09 g, 7.9 mmol) in THF (15 mL) over 20 minutes. After stirring for 5 minutes, the ice bath is removed, and the reaction is stirred for an additional 40 minutes. The reaction is quenched with water, and sodium hydroxide is added. The mixture is stirred for 1 hour and is filtered through Celite and the filtrate evaporated to give trans-2-[4-(pyrimidin-2-ylamino)-cyclohexyl]-ethanol which is used without further purification.

Workup

  1. temperatureis cooled in an ice water bath
  2. customthe ice bath is removed
  3. stirringthe reaction is stirred for an additional 40 minutes
  4. customThe reaction is quenched with water, and sodium hydroxide
  5. additionis added
  6. stirringThe mixture is stirred for 1 hour
  7. filtrationis filtered through Celite
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-3fffdf22a680447cbd57cdce78b2d8df
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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