Aluminium lithium hydride → HCID 178483632, compound

HRID 967156Notes

Reaction equation

HRID 967156 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:16])[CH2:9][CH2:8]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:20]([O:19][C:17](=[O:18])[N:15]([CH2:14][CH2:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][CH2:5][CH2:4][OH:3])[CH2:12][CH2:11]1)[CH3:16])([CH3:21])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178471543HCID 178471543, compound

Product 1

HCID 178483632HCID 178483632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-3-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-propionic acid ethyl ester in 40 ml of tetrahydrofuran was added under ice-cooling 547 mg (14.0 mmol) of lithium aluminium hydride in small portions. The reaction mixture was then stirred for 1 hour at room temperature. To destroy the excess of lithium aluminium hydride, 50 ml of brine was added to the reaction mixture under ice-cooling. It was then partitioned between ether and water, the organic layer was dried over magnesium sulfate and concentrated under reduced pressure giving 3.35 g (100% over 2 stepts) nearly pure trans-{2-[4-(3-hydroxy-propyl)-cyclohexyl]-ethyl}-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS. 317 (MNH4+).

Workup

  1. customTo destroy the excess of lithium aluminium hydride, 50 ml of brine
  2. additionwas added to the reaction mixture under ice-
  3. temperaturecooling
  4. customIt was then partitioned between ether and water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d572f9ddb2b3486c9e4c0a47e4882b95
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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