Ethyl chloroformate → Ethyl (2s)-2-(4-fluorophenyl)morpholine-4-carboxylate

HRID 1671479Notes

Reaction equation

HRID 1671479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10](CC3C=CC=CC=3)[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 12002488(S)-4-Benzyl-2-(4-fluorophenyl)morpholine

Product 1

HCID 67352736Ethyl (2s)-2-(4-fluorophenyl)morpholine-4-carboxylateYield 125.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of (2S)-2-(4-fluorophenyl)-4-(benzyl)morpholine (1.00 g, 3.67 mmol) in toluene (10 mL) was added a solution of ethyl chloroformate (0.39 mL, 4.04 mmol) in toluene (5 mL) at 89° C. The mixture was stirred for 3 hrs and the solvent was evaporated to give ethyl (S)-2-(4-fluorophenyl)morpholine-4-carboxylate (1.17 g) as a black oil.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-38b2732da1084e34b1071b392a6708ff
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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