Acetaldehyde → (S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

HRID 1476311Notes

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+]>CO.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

Conditions

Temperature: 0 °C

Procedure

A solution of (S)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (1.0 g, 4.62 mmol) in MeOH (15 ml) was treated with acetaldehyde (0.204 g, 4.62 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and sodium triacetoxyborohydride (2.450 g, 11.56 mmol) was added all at once. The resulting mixture was stirred for 24 h and the mixture was diluted with DCM (15 ml) and washed with saturated aq. sodium bicarbonate (15 ml). The organic phase dried over sodium sulfate, filtered, and concentrated under pressure to give a residue which was purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→20% MeOH in DCM) to give (S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 86, STEP 1).

Workup

stirringThe resulting mixture was stirred for 24 h
washwashed with saturated aq. sodium bicarbonate (15 ml)
dry with materialThe organic phase dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under pressure
customto give a residue which
customwas purified by column chromatography (ISCO, 12 g silica gel column, eluting with 0→20% MeOH in DCM)

Sources & evidence

ORD record: ord-c3c371146f60479dad0232dfb242e8fa
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018381B2

Reaction notes

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