Toluene → (3R)-1-((1R,2R)-2-Hydroxycyclohex-1-yl)-2,5-dioxopyrrolidin-3-yl acetate

HRID 1918271Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[CH2:9][C:8](=[O:10])[N:7]([C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[O:17]CC2C=CC=CC=2)[C:6]1=[O:25])(=[O:3])[CH3:2].C1(C)C=CC=CC=1>[Pd]>[C:1]([O:4][C@@H:5]1[CH2:9][C:8](=[O:10])[N:7]([C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[OH:17])[C:6]1=[O:25])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of (3R)-1-((1R,2R)-2-benzyloxycyclohex-1-yl)-2,5-dioxopyrrolidin-3-yl acetate (3a) in toluene (446 g, 0.151 mol) was added 10% Pd/C (6.3 g, 50 wt-% water wet), and the reaction vessel was flushed twice with H2. The reaction mixture was agitated at 18° C. under H2 (5 bar) for 8 hours and at 45° C. under H2 (5 bar) for 15.5 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was filtered, the filtrate was washed with toluene and the filtrate was concentrated in vacuo to give 3-(R)-1-[(1R,2R)-2-hydroxycyclohexyl]-2,5-dioxopyrrolidin-3-yl acetate (4a) as a white hygroscopic foam (46.0 g).

Workup

customthe reaction vessel was flushed twice with H2
filtrationThe reaction mixture was filtered
washthe filtrate was washed with toluene
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-cd8a5289aef54352acca08f1cf832074
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618311B2

Reaction notes

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