Tert-butyl 4-hydroxypiperidine-1-carboxylate → 4-[4-(4,4,4-Trifluoro-butyl)-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1022875Notes

Reaction equation

HRID 1022875 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[C:5]2[CH2:12][CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16].[C:19]([N:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].N(C([O-])=O)=NC([O-])=O>O1CCCC1>[C:22]([O:21][C:19]([N:26]1[CH2:31][CH2:30][CH:29]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[N:7][CH:6]=[C:5]3[CH2:12][CH2:13][CH2:14][C:15]([F:18])([F:16])[F:17])[CH2:28][CH2:27]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 51573101N-carboxylatoiminocarbamateHCID 1360928996-Hydroxy-4-(4,4,4-trifluoro-butyl)-isoquinoline

Product 1

HCID 576468604-[4-(4,4,4-Trifluoro-butyl)-isoquinolin-6-yloxy]-piperidine-1-carboxylic acid tert-butyl esterYield 26.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg of compound 88, 118 mg of Boc-(4-hydroxy)piperidine and 416 mg of Diphenyl-[4-[1H,1H,2H,2H-perfluorodecyl]phenyl]phosphine were dissolved in 5 mL of dry tetrahydrofuran. 208 mg of Bis (1H, 2H, 2H, 3H, 3H-perfluorononyl)-azodicarboxylate were added and the reaction was allowed to stir overnight. The mixture was evaporated to dryness and filtered over a 5 g Fluoro-Flash cartridge. The obtained crude product was purified by preparative HPLC to yield 46 mg of the desired product.

Workup

  1. customThe mixture was evaporated to dryness
  2. filtrationfiltered over a 5 g Fluoro-Flash cartridge
  3. customThe obtained crude product
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-7bd940f400c241d9aba34bb1efc3f850
Source dataset
uspto-grants-2014_05
Patent number
US08722671B2

Reaction notes

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