Ammonium Chloride → (2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinemethanol

HRID 2367549Notes

Reaction equation

HRID 2367549 reaction equation
[C:1]1([CH2:7][NH:8][C@H:9]([CH2:12][CH3:13])[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([C@@H:16]1[O:18][CH2:17]1)Cl.Cl([O-])(=O)(=O)=O.[Li+].[O-]CC.[Na+].[NH4+].[Cl-]>ClCCCl>[CH2:12]([C@H:9]1[N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14][C@@H:16]([CH2:17][OH:18])[O:11][CH2:10]1)[CH3:13]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 927306(R)(-)-2-Benzylamino-1-butanolHCID 2723922Sodium ethoxideHCID 2734062(-)-EpichlorohydrinHCID 23665649Lithium perchlorate

Product 1

HCID 51357958(2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinemethanolYield 122.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2R)-2-[(phenylmethyl)amino]-1-butanol (10.06 g, 56.1 mmol) in 1,2-dichloroethane (DCE) (250 mL) was added (R)-(−)-epichlorohydrin (6.75 g, 72.9 mmol) followed by lithium perchlorate (5.97 g, 56.1 mmol) under nitrogen. The reaction was stirred for 2 days at room temperature, then sodium ethoxide (52.4 mL, 140 mmol) was added and the reaction continued to stir for 3 days. Saturated NH4Cl was added, and the product was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to afford the title compound (16.2 g) as a colorless oil. LC-MS (ES) m/z=236 [M+H]+.

Workup

  1. stirringto stir for 3 days
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-79e6a6cac85542b285769cc18ebbda4c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…