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

HRID 1771206Notes

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-2969e99b97524891a8f9e1a38c7cf4e1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248140B2

Reaction notes

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