6-Oxabicyclo[3.1.0]hexane → HCID 86713721, compound

HRID 1406056Notes

Reaction equation

HRID 1406056 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=1.[CH:11]12[O:16][CH:15]1[CH2:14][CH2:13][CH2:12]2>>[F:10][C:5]1[CH:4]=[C:3]([CH:8]=[C:7]([F:9])[CH:6]=1)[CH2:2][C@@H:14]1[CH2:13][CH2:12][CH2:11][C@H:15]1[OH:16]

Participants

3

Reactant 2

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 5188963,5-Difluorobenzyl bromide

Product 1

HCID 86713721HCID 86713721, compound

Procedure

Reaction of the Grignard reagent prepared from 1-(bromomethyl)-3,5-difluorobenzene with 6-oxabicyclo[3.1.0]hexane gave trans-2-(3,5-difluorobenzyl)cyclopentanol. Conversion to the mesylate, followed by displacement with sodium azide and reduction with triphenylphosphine afforded cis-2-(3,5-difluorobenzyl)cyclopentanamine.

Sources & evidence

ORD record
ord-8ef59a6438e74366bf7d21311d49e1fc
Source dataset
uspto-grants-2014_12
Patent number
US08916564B2

Reaction notes

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