Sodium Hydroxide → HCID 178511560, compound

HRID 1506248Notes

Reaction equation

HRID 1506248 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8](O)=[O:9])[CH2:4][CH2:3]1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].C1(C)C=CC=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][OH:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67340441Sodium bis(2-methoxyethoxy)aluminum hydride tolueneHCID 178511567HCID 178511567, compound

Product 1

HCID 178511560HCID 178511560, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

trans-4-Aminocyclohexanecarboxylic acid (314 mg, 2.19 mmol) was gradually added to sodium bis(2-methoxyethoxy)aluminum hydride-toluene solution (65 wt %, 3.0 mL) in toluene (3 mL) at 75° C., and the reaction mixture was stirred for 7 hours. The reaction mixture was allowed to cool to room temperature and stirred with 1 M aqueous sodium hydroxide (20 mL) at 80° C. for 10 minutes. The reaction mixture was allowed to cool to room temperature and partitioned between water and toluene, and the aqueous layer was extracted with chloroform three times. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a colorless solid (170 mg, yield 60%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water and toluene
  3. extractionthe aqueous layer was extracted with chloroform three times
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ddcd669bfaa4efbbd46106b0b417c1b
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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