Water → HCID 178474987, compound

HRID 1664988Notes

Reaction equation

HRID 1664988 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:14][CH2:13]1)C.O.[OH-].[Na+]>C1COCC1>[OH:9][CH2:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:21])[CH3:20])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178471808HCID 178471808, compound

Product 1

HCID 178474987HCID 178474987, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAlH4 (2.10 g, 55 mmol) and THF (150 ml) were placed in a dry balloon. After cooling this mixture to 0° C. a solution of (trans-4-acetylamino-cyclohexyl)-acetic acid ethyl ester (8.42 g, 37 mmol) in little THF was added dropwise. The reaction was stirred 1 h before careful neutralization with H2O (5.6 ml), 1 N NaOH (3×5.6 ml) and more H2O (5.6 ml). The resulting mixture was stirred over night before filtering off the solids. Evaporation of the solvent and drying under high vacuum afforded 5.25 g (76%, 28 mmol) of a light brown solid. MS (m/z): 186.4 ([M+H+).

Workup

  1. additionwas added dropwise
  2. filtrationbefore filtering off the solids
  3. customEvaporation of the solvent
  4. customdrying under high vacuum

Sources & evidence

ORD record
ord-d69b9969585c49dca1c9afbbf4d72872
Source dataset
uspto-grants-2011_10
Patent number
US08039490B2

Reaction notes

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