Aluminium lithium hydride → (3-(2-Amino-4-chlorophenoxy)cyclopentyl)methanol

HRID 1773587Notes

Reaction equation

HRID 1773587 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[NH2:25])[CH2:13]1)=O)C>O1CCCC1>[NH2:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[O:17][CH:14]1[CH2:15][CH2:16][CH:12]([CH2:10][OH:9])[CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 580563063-(2-Amino-4-chloro-phenoxy)-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 58056289(3-(2-Amino-4-chlorophenoxy)cyclopentyl)methanolYield 105.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (1 M, 3 mL) was added to a cooled (0° C.) solution of 3-(2-amino-4-chloro-phenoxy)-cyclopentanecarboxylic acid ethyl ester (0.2 g) in tetrahydrofuran (5 mL) and the resulting mixture was stirred for 30 minutes. The reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride and filtered. The filter cake was washed with ethyl acetate and the filtrate was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 180 mg of [3-(2-amino-4-chloro-phenoxy)-cyclopentyl]-methanol without further purifications.

Workup

  1. customThe reaction mixture was then quenched by addition of a saturated aqueous solution of ammonium chloride
  2. filtrationfiltered
  3. washThe filter cake was washed with ethyl acetate
  4. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57337be362c24a35964933c1418d25a5
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…