Sodium Chloride → HCID 18187489, compound

HRID 1386769Notes

Reaction equation

HRID 1386769 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][C:23]([F:31])([F:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C([O-])(O)=O.[Na+].[OH-].[Na+].[Na+].[Cl-]>C(Cl)Cl.O.CCOCC>[F:31][C:23]([F:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][CH2:21][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Participants

9

Reactant 5

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18187485HCID 18187485, compound

Product 1

HCID 18187489HCID 18187489, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (2.5 mL, 3.7 g, 32 mmol) was added dropwise to a solution of 1-(t-butoxycarbonyl)-4-(3,3-difluoro-3-phenylpropyl)piperidine (42 mg, 0.12 mmol, from EXAMPLE 154, Step C) in CH2Cl2 (2.5 mL) at 0° C. After 80 min., the solution was transferred using a double-ended needle to a rapidly stirred solution of NaHCO3 (5.0 g, 60 mmol) in H2O (50 mL). Ether (50 mL) and 2.5 N NaOH (20 mL) were added, followed by solid NaCl to saturate the aqueous layer. The aqueous layer was separated and extracted with ether (50 mL). The organic layers were washed in succession with saturated aq. NaCl (20 mL), combined, dried (Na2SO4), decanted,and evaporated to give the title compound as 27 mg of colorless oil. 1H NMR (400 MHz, CD3OD) δ 7.51-7.40 (m, 5H), 2.98 (dm, J=12,22H), 2.53 (td, J=12, 3, 2H), 2.24-2.10 (m, 2H), 1.65 (bd, J=12, 2H), 1.42-1.26 (m, 3H), 1.06 (qd, J=12,4,2H); ESI-MS 240 (M+H); HPLC A: 2.25 min.

Workup

  1. concentrationto saturate the aqueous layer
  2. customThe aqueous layer was separated
  3. extractionextracted with ether (50 mL)
  4. washThe organic layers were washed in succession with saturated aq. NaCl (20 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6f07b499fd6f43a6a48e53e2b0596e82
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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