3-Fluorophenol → (S)-tert-butyl 2-((3-fluorophenoxy)methyl)pyrrolidine-1-carboxylate

Reaction equation

[OH:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[F:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1>>[F:15][C:16]1[CH:21]=[C:20]([CH:19]=[CH:18][CH:17]=1)[O:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

Reactant 2

HCID 97433-Fluorophenol

HCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 22857712(S)-tert-butyl 2-((3-fluorophenoxy)methyl)pyrrolidine-1-carboxylateYield 81.7%

Procedure

The title compound (D44) (239.7 mg) was prepared according to the experimental procedure described in Description 40 starting from (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate (D43) (200 mg, 0.993 mmol) and 3-Fluorophenol (0.089 ml, 0.993 mmol).

Sources & evidence

ORD record: ord-7ffd1dcb244f4c688bb47e121eafc8ca
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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