Acetaldehyde → (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate
Reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH:16](=O)[CH3:17].[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:20].[Na+]>C(Cl)Cl>[CH2:19]([N:1]([CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:16][CH3:17])[CH3:20]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A solution of (R)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (commercially available, 250 mg, 1.16 mmol) and DCM (7 ml) at 0° C. was treated with acetaldehyde (0.162 ml, 2.89 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and sodium triacetoxyborohydride (612 mg, 2.89 mmol) was added all at once. The resulting mixture was stirred for 24 h and the mixture was diluted with 20 ml of DCM (20 ml) and washed with saturated aq. sodium bicarbonate (20 ml). The organic phase was dried over sodium sulfate, filtered, and concentrate under pressure to give (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 90, STEP 1)
Workup
- stirringThe resulting mixture was stirred for 24 h
- washwashed with saturated aq. sodium bicarbonate (20 ml)
- dry with materialThe organic phase was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrate under pressure
Sources & evidence
- ORD record
- ord-778e7ce377ba4ba1a4b59d088682ef87
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248140B2
Reaction notes
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