Ammonium formate → 2-(1,2-Diphenyl-ethyl)-morpholine

HRID 736037Notes

Reaction equation

HRID 736037 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd]>[C:22]1([CH:14]([CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 689010384-Benzyl-2-(1,2-diphenyl-vinyl)-morpholine

Product 1

HCID 111498202-(1,2-Diphenyl-ethyl)-morpholine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a methanolic solution of 4-Benzyl-2-(1,2-diphenyl-vinyl)-morpholine (4.9 g, 13.9 mmol) is added ammonium formate (14 g, 222.2 mmol) and 10% Pd—C (5 g). The reaction is stirred under nitrogen and heated at reflux for 30 min then cooled to room temperature and filtered through Celite®. The filtrate is concentrated under reduced pressure and the residue is taken up in methanol and purified by cationic ion exchange resin SCX-2® chromatography. The purified residue (2.9 g, 80%) comprises a 3:1 ratio of diastereoisomers.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 min
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. custompurified by cationic ion exchange resin SCX-2® chromatography

Sources & evidence

ORD record
ord-553c4e30e897480099553fc6fb0ea427
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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