Triethylamine → tert-Butyl [(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]carbamate

HRID 2367042Notes

Reaction equation

HRID 2367042 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[N:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]([N:20]2[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21]2)=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:4]1[N:3]=[C:2]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]([N:20]3[CH2:24][CH2:23][C@H:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:21]3)=[O:19])[CH2:16][CH2:17]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 6023342-Chloro-6-(trifluoromethyl)pyridineHCID 57803247tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamate

Product 1

HCID 57803327tert-Butyl [(3S)-1-({1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}carbonyl)pyrrolidin-3-yl]carbamateYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-6-(trifluoromethyl)pyridine (1.8 g, 9.9 mmol), tert-butyl [(3S)-1-(piperidin-4-ylcarbonyl)pyrrolidin-3-yl]carbamate (2.97 g, 10.0 mmol) and triethylamine (4.1 mL, 30 mmol) in DMF (50 mL) was heated at 100° C. for 4 hrs. After cooling down, ethyl acetate was added. The resulting solution was washed with brine several times, dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel to give the title compound (1.3 g) as a yellow solid. MS (M+H) 443.2.

Workup

  1. temperatureAfter cooling down
  2. washThe resulting solution was washed with brine several times
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0259c53cb69d4ade8e1532a340f8e912
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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