Potassium cyanate → 1-((3S,4R)-1-methyl-4-phenylpyrrolidin-3-yl)urea

HRID 588102Notes

Reaction equation

Cl.[CH3:2][N:3]1[CH2:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([NH2:14])[CH2:4]1.[O-:15][C:16]#[N:17].[K+]>Cl>[CH3:2][N:3]1[CH2:7][C@@H:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:5]([NH:14][C:16]([NH2:17])=[O:15])[CH2:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

(3S,4R)-1-Methyl-4-phenylpyrrolidin-3-amine hydrochloride (556 mg, 2.231 mmol) was dissolved in HCl (2 N, 4 mL) and potassium cyanate (905 mg, 11.16 mmol) was added. The reaction mixture was stirred at 80° C. for 3 h. The reaction was quenched with sat. sodium bicarbonate and extracted with EtOAc followed by 3:1 chloroform/IPA. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give 1-((3S,4R)-1-methyl-4-phenylpyrrolidin-3-yl)urea, which was carried onto the next step without further purification. MS ESI calc'd. For C12H17N3O [M+1]+ 220. found 220.

Workup

customThe reaction was quenched with sat. sodium bicarbonate
extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-84483412d59f4d55860f0cfe282f975a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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