Benzyl Bromide → (2R,3S)-benzyl 4-benzyl-2-methyl-5-oxomorpholine-3-carboxylate

HRID 524598Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C@H:10]([CH3:15])[C@H:9]1[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][C@H:10]([CH3:15])[C@H:9]1[C:16]([O:18][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of (2R,3S)-4-benzyl-2-methyl-5-oxomorpholine-3-carboxylic acid (1.07 g, 4.25 mmol) (The compound was synthesized according to the procedure as described in Helvetica Chimica Acta, 87, 2004), (bromomethyl)benzene (0.87 g, 5.1 mmol) and potassium carbonate (1.16 g, 8.5 mmol) in acetonitrile (20 mL) was stirred at 65° C. for 6 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=4/1) to give the title compound as colorless oil (1.23 g, 85%). The compound was characterized by the following spectroscopic data:

Workup

customwas synthesized
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=4/1)

Sources & evidence

ORD record: ord-a76aba52635c475288f46cf102128725
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340538B2

Reaction notes

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