Hydrochloric Acid → HCID 86680030, compound

HRID 1915820Notes

Reaction equation

HRID 1915820 reaction equation
C([N:8]1[CH2:14][CH2:13][CH:12]([OH:15])[C:11]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])([CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[F:22][C:19]([F:20])([F:21])[C:18]([NH:17][C:11]1([CH3:16])[CH:12]([OH:15])[CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1)=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86680029HCID 86680029, compound

Product 1

HCID 86680030HCID 86680030, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(1-benzyl-5-hydroxy-4-methylazepan-4-yl)-2,2,2-trifluoroacetamide (1.7 g, 5.0 mmol) in MeOH (30 mL) was added 1M HCl (1 mL) and palladium hydroxide on carbon (0.25 g). The mixture was shaken under an atmosphere of hydrogen gas (40 psi) for 72 hr. The mixture was filtered through Celite® washing with MeOH (30 mL). The solvent was removed under reduced pressure and the residue passed through an SCX column eluting with (1-10% (7 M NH3 in MeOH)/DCM) to give 2,2,2-trifluoro-N-(5-hydroxy-4-methylazepan-4-yl)acetamide as a yellow gum (0.8 g, 66%). 1H (400 MHz, CDCl3) δ 6.90 (br s, 1H), 4.22-4.16 (m, 1H), 3.70-3.60 (m, 1H), 3.40-3.35 (m, 1H), 3.15-2.99 (m, 1H), 2.90-2.75 (m, 2H), 2.20-2.05 (m, 1H), 1.99-1.75 (m, 4H), 1.53 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashing with MeOH (30 mL)
  3. customThe solvent was removed under reduced pressure
  4. washeluting with (1-10% (7 M NH3 in MeOH)/DCM)

Sources & evidence

ORD record
ord-07ddf44aae014d85a6ee91f91aca3bbe
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

Loading…