Methanol → HCID 89726545, compound

HRID 926349Notes

Reaction equation

HRID 926349 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[O:10][CH2:9][C:8](=O)[N:7]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:5])[CH3:2].CO>O1CCCC1.ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[O:10][CH2:9][CH2:8][N:7]1[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 89726767HCID 89726767, compound

Product 1

HCID 89726545HCID 89726545, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-benzyl-2-methyl-5-oxo-morpholine-3-carboxylic acid ethyl ester (0.24 g, 0.865 mmol; prepared according to the procedure described in Meinzer A. et al., Helv. Chim. Acta 2004, 87, 90-105) in tetrahydrofuran (7 ml) was cooled to −20° C. and borane-methyl sulfide complex (0.246 ml, 2.595 mmol) was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred overnight. After the addition of methanol (5 ml), stirring was continued for 1 h. The solution was diluted with dichloromethane, washed with brine, and concentrated in vacuo. The resulting 4-benzyl-2-methyl-morpholine-3-carboxylic acid ethyl ester was used in the next step without further purification. LC/MS (method 8): Rt=0.54 min; m/z=264.25 (M+H+).

Workup

  1. customprepared
  2. additionborane-methyl sulfide complex (0.246 ml, 2.595 mmol) was added dropwise
  3. stirringstirring
  4. waitwas continued for 1 h
  5. washwashed with brine
  6. concentrationconcentrated in vacuo
  7. customThe resulting 4-benzyl-2-methyl-morpholine-3-carboxylic acid ethyl ester was used in the next step without further purification

Sources & evidence

ORD record
ord-3d77562a6db74185a43dc6b972160911
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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