Water → HCID 86709202, compound

HRID 1851143Notes

Reaction equation

HRID 1851143 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]([CH3:17])[C@:10]([CH3:16])([OH:15])[C:11]([F:14])([F:13])[F:12])C1C=CC=CC=1.O>CO>[NH2:8][C@H:9]([CH3:17])[C@:10]([CH3:16])([OH:15])[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 962WaterHCID 86709200HCID 86709200, compound

Product 1

HCID 86709202HCID 86709202, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,3R)-3-(Dibenzylamino)-1,1,1-trifluoro-2-methylbutan-2-ol (Example 52B) (1.94 g, 5.75 mmol) was dissolved in MeOH (50 mL) and an then treated with the catalyst (0.612 g, 10% dry weight, 50% water). The reaction vessel was then purged with alternating vacuum and N2 (7×). H2 was introduced and then the vessel was purged again with vacuum alternated with H2 (3×). The reaction vessel was then finally charged with H2 (90 psi). The pressure was allowed to drop to ca. 80 psi and allowed to stay there overnight (H2 uptake appeared to stop). After 15 h, the reaction was purged with N2/vacuum cycles and the catalyst/carbon was removed by filtration through celite. The celite cake was rinsed with MeOH and the resulting filtrate was carefully concentrated to a white solid by rotavap followed by finishing the last part of the liquid volume with an N2 blow down. The resulting grey solid/film was dissolved in CH2Cl2 and then filtered through a microfilter to remove remaining Pd/C. The resulting pale yellow filtrate was then blown down and exposed to light vacuum to afford a pale yellow solid (0.726 g, 80%) PMR of this material showed excellent purity and no remaining sm: 1H NMR (400 MHz, DMSO-d6) δ 2.95 (q, J=6.7 Hz, 1H), 1.60 (bs, 2H), 1.13-1.11 (m, 3H), 0.96-0.94 (m, 3H).

Workup

  1. customThe reaction vessel was then purged
  2. additionH2 was introduced
  3. customthe vessel was purged again with vacuum
  4. additionThe reaction vessel was then finally charged with H2 (90 psi)
  5. waitAfter 15 h
  6. customthe reaction was purged with N2/vacuum cycles
  7. customthe catalyst/carbon was removed by filtration through celite
  8. washThe celite cake was rinsed with MeOH
  9. concentrationthe resulting filtrate was carefully concentrated to a white solid by rotavap
  10. dissolutionThe resulting grey solid/film was dissolved in CH2Cl2
  11. filtrationfiltered through a microfilter
  12. customto remove

Sources & evidence

ORD record
ord-3330406260144e77aeb94143900d4cf4
Source dataset
uspto-grants-2015_02
Patent number
US08957104B2

Reaction notes

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