Borane → HCID 86671745, compound

HRID 595016Notes

Reaction equation

HRID 595016 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([F:25])=[C:16]([C:20]([F:24])=[C:21]([F:23])[CH:22]=2)[C:17](O)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[F:25][C:15]1[C:16]([CH2:17][OH:18])=[C:20]([F:24])[C:21]([F:23])=[CH:22][C:14]=1[N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 86671744HCID 86671744, compound

Product 1

HCID 86671745HCID 86671745, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2,5,6-trifluorobenzoic acid (0.84 g) was reacted in the standard reduction conditions with Borane in THF (see Example 179, Step i). The crude product was purified by Flash chromatography using a gradient of Hexane/Ethyl acetate (from 9:1 to 1:4) to give tert-butyl 4-(2,4,5-trifluoro-3-(hydroxymethyl)phenyl)piperazine-1-carboxylate as a white solid (0.18 g, 37% yield from beginning of step ii)

Workup

  1. customThe crude product was purified by Flash chromatography

Sources & evidence

ORD record
ord-f08a500bcfcc4b30b92492a8f4d1681a
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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