Hydrochloric Acid → 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester

HRID 22969Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4](/[CH:7]=[CH:8]/[C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[N:3]1[CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.Cl>C1(C)C=CC=CC=1.CO>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][S:18][CH2:17][CH2:16][N:3]1[C:2](=[O:1])[CH2:6][CH2:5][C@@H:4]1/[CH:7]=[CH:8]/[C@@H:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of methyl 4-[(2-{(5R)-2-oxo-5-[(1E)-3-oxooct-1-enyl]pyrrolidin-1-yl}ethyl)thio]-butanoate (0.039 g, 0.1 mmol) in 2 mL of anhydrous toluene was added dropwise to a −30° C. solution of (R)-2-methyl-CBS-oxazaborolidine (1 M in toluene, 0.05 mL, 0.05 mmol) and borane-methyl sulfide complex (10 M, 0.01 mL, 0.1 mmol). The reaction was stirred for 7 hours at −30° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via chromatography yielding 11 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester as an oil. This was taken directly on to the next step.

Workup

temperatureThe solution was warmed to room temperature
customthe solvents were removed via reduced pressure
customThe crude residue was purified via chromatography

Sources & evidence

ORD record: ord-8aa5e02b8b4542b18d3d5fa4e489be9c
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849657B2

Reaction notes

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