Triethylamine → HCID 66841547, compound

HRID 1929007Notes

Reaction equation

HRID 1929007 reaction equation
O[C@H:2](C)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][CH2:5]1.[CH2:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[C:40]([O:44][C:45](=[O:53])[NH:46][CH:47]1CCNCC1)([CH3:43])([CH3:42])[CH3:41]>C(Cl)Cl>[C:40]([O:44][C:45]([NH:46][CH:47]1[CH2:24][CH2:23][N:20]([CH2:18][C@@H:3]([N:4]2[CH2:5][CH2:6][CH:7]([O:10][C:11](=[O:16])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:8][CH2:9]2)[CH3:2])[CH2:21][CH2:22]1)=[O:53])([CH3:43])([CH3:42])[CH3:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 7238334-(N-Boc-amino)piperidineHCID 675236702,2-Dimethyl-propionic acid 1-((R)-2-hydroxy-propyl)-piperidin-4-yl ester

Product 1

HCID 66841547HCID 66841547, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of alcohol 53 (1.26 g, 5.16 mmol) and triethylamine (1.43 ml, 10.32 mmol) in 80 ml of DCM is cooled to −78 C. Triflic anhydride (0.85 ml, 5.16 mmol) is slowly added and stirring continued for 1 hour. The mixture is then allowed to warm up to 0 C and cooled back to −78 C after 15 minutes. A solution of piperidin-4-yl-carbamic acid tert-butyl ester, 3, (1.03 g, 5.16 mmol) in 40 ml of DCM is slowly added at −78 C. After complete addition, the cooling bath is removed and the dark solution is allowed to warm up to room temperature. The mixture is washed twice with water, dried over sodium sulphate, filtered and evaporated. The crude is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (1%).

Workup

  1. temperatureto warm up to 0 C
  2. temperaturecooled back to −78 C after 15 minutes
  3. additionAfter complete addition
  4. customthe cooling bath is removed
  5. washThe mixture is washed twice with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-42a1a9978a10405e8173488469b0d5a8
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

Loading…