5-Bromo-2-methoxyphenol → (3S)-3-(5-Bromo-2-methoxyphenoxy)-1-methylpyrrolidine

Reaction equation

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

Participants

Reactant 2

HCID 1422285-Bromo-2-methoxyphenol

HCID 6435041-Methyl-3-pyrrolidinol, (+)-

Product 1

HCID 66824451(3S)-3-(5-Bromo-2-methoxyphenoxy)-1-methylpyrrolidineYield 30.5%

Procedure

The title compound was prepared by the method outlined for Preparative Example 63 using 5-bromo-2-methoxy-phenol (1.00 g, 4.93 mmol) and (S)-1-methyl-pyrrolidin-3-ol (593 mg, 5.86 mmol) to afford titled compound as a colorless solid (430 mg, 30%). LC/MS (Method B) 1.17 min, [M+1]+ 286/288.

Workup

customThe title compound was prepared by the method

Sources & evidence

ORD record: ord-66bc8419a9a3432087c49c0b705dc6d2
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927546B2

Reaction notes

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