Aluminate(1-), tetrahydro-, (T-4)- → HCID 67434585, compound

HRID 1486808Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:15][NH:14][C:13](=O)[C@H:12]([CH3:17])[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[AlH4-].[OH-].[Na+].O=[Si]=O>C1COCC1.O>[CH2:1]([O:8][CH2:9][C@H:10]1[O:11][C@@H:12]([CH3:17])[CH2:13][NH:14][CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of (2S,6S)-6-((benzyloxy)methyl)-2-methylmorpholin-3-one (6.12 g, 0.026 mol) in THF (20 mL) under a nitrogen atmosphere at rt was added 1 M tetrahydroaluminate in THF (30 mL, 0.030 mol) dropwise over a 15-min period. The reaction mixture was stirred for 2.5 h after which time it was cooled to 0° C. followed by the slow addition of water (13 mL) and then 1 N aq. NaOH (0.9 mL). The quenched reaction was stirred until the precipitate became granular after which time Celite 545 (10 g) was added followed by filtering over a Celite pad and rinsing three times with DCM (30 mL) and ethyl ether (30 mL). The combined filtrates were concentrated and purified over silica gel (Biotage, eluting with a gradient of 0-5% MeOH in DCM) to provide (2S,6S)-2-((benzyloxy)methyl)-6-methylmorpholine (2.7 g, 0.012 mol, 46.2% yield) after combining the desired fractions, concentration and drying in vacuo.

Workup

customThe quenched reaction
stirringwas stirred until the precipitate
additionwas added
filtrationby filtering over a Celite pad
washrinsing three times with DCM (30 mL) and ethyl ether (30 mL)
concentrationThe combined filtrates were concentrated
custompurified over silica gel (Biotage
washeluting with a gradient of 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-de52d1e46f6f47f7b7b7993654185965
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428495B2

Reaction notes

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