Trifluoroacetic acid → (R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine

HRID 872200Notes

Reaction equation

HRID 872200 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C@@H:21]2[O:39][C:24]3=[CH:25][N:26]=[C:27]([C:29]4[CH2:30][CH2:31][N:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH2:33][CH:34]=4)[CH:28]=[C:23]3[CH2:22]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[CH3:38][S:35]([N:32]1[CH2:31][CH:30]=[C:29]([C:27]2[CH:28]=[C:23]3[CH2:22][C@H:21]([CH:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]4)[O:39][C:24]3=[CH:25][N:26]=2)[CH2:34][CH2:33]1)(=[O:36])=[O:37]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71208290HCID 71208290, compound

Product 1

HCID 71208337(R)-5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-piperidin-4-yl-2,3-dihydro-furo[2,3-c]pyridine

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Trifluoroacetic acid (2 mL) is added to a solution of (R)-4-[5-(1-methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.0 g) in dichloromethane (10 mL) at room temperature. The solution is stirred at room temperature overnight and then diluted with dichloromethane, 2 N aqueous NaOH solution, and saturated aqueous Na2CO3 solution. The resulting mixture is vigorously stirred for 20 min and then extracted with dichloromethane. The combined extract is dried (Na2SO4) and concentrated to give the title compound. Mass spectrum (ESI+): m/z=364 [M+H]+.

Workup

  1. stirringThe resulting mixture is vigorously stirred for 20 min
  2. extractionextracted with dichloromethane
  3. extractionThe combined extract
  4. dry with materialis dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a155cdebad54860ba055472dd3ebcb6
Source dataset
uspto-grants-2015_03
Patent number
US08975277B2

Reaction notes

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