Reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(O)(O[CH2:19][CH2:20][NH2:21])(=O)=O>O.CO.C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][C@@H:10]1[O:11][CH2:19][CH2:20][NH:21][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Conditions
- Temperature
- 40 °C
Procedure
To a stirred mixture of (R)-2-(benzyloxymethyl)oxirane (10.0 g, 60.9 mmol) and NaOH (19.49 g, 487.2 mmol) in H2O (46 mL) and MeOH (18 mL), there was added 2-aminoethyl hydrogen sulfate (36.8 g, 255.8 mmol) in portions. After addition, the reaction mixture was stirred at 40° C. for 2 h. After cooling, the mixture was treated with NaOH (15.0 g, 375.0 mmol) then toluene (70 mL) and stirred at 65° C. overnight. The mixture was cooled, diluted with toluene (27 mL) and H2O (92 mL). The toluene layer was separated and the aqueous layer was extracted with CH2Cl2 (2×50 mL). The combined organic layers were concentrated to give crude (R)-2-(benzyloxymethyl)morpholine (˜14 g), which was used without purification. MS m/z 208 (M+H+).
Workup
- additionAfter addition
- temperatureAfter cooling
- temperatureThe mixture was cooled
- customThe toluene layer was separated
- extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
- concentrationThe combined organic layers were concentrated
Sources & evidence
- ORD record
- ord-f2174912797947ce8fd1a405456fe6e4
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872028B2
Linked notes
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