(R)-beta-aminophenethyl alcohol → HCID 90025824, compound

HRID 59690

Reaction equation

[CH3:1][CH:2]([CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([O:5]N1C(=O)CCC1=O)=O.[CH:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:31])[CH2:29][OH:30])=[CH:24][CH:23]=1>C1COCC1>[OH:30][CH2:29][C@H:28]([NH:31][C:3](=[O:5])[C@@H:2]([CH3:1])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:25]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 48 °C

Procedure

To a solution consisting of (±)-2,5-dioxopyrrolidin-1-yl 2-methyl-5-phenyl pentanoate (18mb(i), 85.6 g, 296 mmol) in THF (3000 mL) at 48° C. was added R-(−)-2-phenylglycinol (65.9 g, 480 mmol, Bridge Organics) in portions. The resulting reaction mixture was stirred at 48° C. for 40 hours. A white precipitate formed, which was filtered from the reaction mixture and washed with THF. The filtrate was concentrated under vacuum and the residue, comprising the diastereomeric pair, was chromatographed on silica gel. Elution with ethyl acetate-heptane (50:50 v/v) afforded the pure diastereomer title compound (31.3 g, 34%) as a colorless solid; TLC Rf 0.205 (solvent system: 50:50 v/v ethyl acetate-heptane); HPLC retention time 15.1 minutes, stationary phase: Gemini 5μ C18 250×4.6 mm, ultraviolet detector at 210 nm, mobile phase: 1 mL/min, 60:40:0.1 v/v methanol-water-acetic acid.

Workup

customThe resulting reaction mixture
customA white precipitate formed
filtrationwhich was filtered from the reaction mixture
washwashed with THF
concentrationThe filtrate was concentrated under vacuum
customwas chromatographed on silica gel
washElution with ethyl acetate-heptane (50:50 v/v)

Sources & evidence

ORD record: ord-845b5e6a71054bcaa8d4933eb583801c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440919B2

Linked notes

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