Sodium Hydroxide → HCID 18187445, compound

HRID 1386775Notes

Reaction equation

HRID 1386775 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([F:25])([F:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.I[Si](C)(C)C.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[F:25][C:16]([F:24])([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 18187703HCID 18187703, compound

Product 1

HCID 18187445HCID 18187445, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

1-(t-Butoxycarbonyl)-4-(3,3-difluoro-3-(4-fluorophenyl)propyl)piperidine (122 mg, 0.34 mmol, from EXAMPLE 155, Step G) was dried by evaporation of a toluene solution at reduced pressure. The residue was dissovlved in chloroform (7.6 mL) and iodotrimethylsilane (0.100 mL, 141 mg, 0.70 mmol) was added. After stirring 30 min at RT, the solution was poured into a mixture of saturated aqueous NaHCO3 (15 mL) and 2.5 N NaOH (5 mL), and extracted with ether (50 mL). The organic layer was washed with saturated aq. NaCl (15 ml), dried (Na2SO4), decanted, and evaporated to give the title compound as 88 mg of colorless oil. 1H NMR (500 MHz, CD3OD) δ 7.51 (dd, J=9, 5,22H), 7.17 (t, J=9, 2H), 2.98 (dm, J=12, 2H), 2.52 (td, J=12, 3, 2H), 2.17 (tin, J=16, 2H), 1.65 (bd, J=13, 2H), 1.42-1.26 (m, 3H), 1.07 (qd, J=12, 4, 2H); ESI-MS 258 (M+H); HPLC A: 2.64 min.

Workup

  1. extractionextracted with ether (50 mL)
  2. washThe organic layer was washed with saturated aq. NaCl (15 ml)
  3. dry with materialdried (Na2SO4)
  4. customdecanted
  5. customevaporated

Sources & evidence

ORD record
ord-1acd4adeb7624d00bf2e0b07a1803a84
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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