Borane → Tert-butyl 3-(hydroxymethyl)morpholine-4-carboxylate

HRID 2262471Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

Morpholine-3,4-dicarboxylic acid 4-tert-butyl ester (9.50 g, 41 mmol) was dissolved in anhydrous THF (50 mL) under nitrogen and cooled to −10° C. A 1M solution of borane (82 mL, 82 mmol) was added dropwise whilst maintaining the temperature below 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to −5° C. and water (10 mL) was added cautiously followed by Na2CO3 (9.5 g) in water (20 mL). After stirring for 30 min at room temperature the THF was removed in vacuo, water was added and the reaction mixture was extracted with diethylether (×3). The combined organic extracts were dried (MgSO4) and the solvent was evaporated in vacuo to give 3-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (8.9 g, 100%) as a colourless oil.

Workup

temperaturewhilst maintaining the temperature below 0° C
temperatureto warm to room temperature
temperatureThe reaction mixture was cooled to −5° C.
customwas removed in vacuo, water
additionwas added
extractionthe reaction mixture was extracted with diethylether (×3)
dry with materialThe combined organic extracts were dried (MgSO4)
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-157b816ff91f4ae4b942e39aa6da8276
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851471B2

Reaction notes

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