Sodium Hydroxide → (S)-1-(2-(2-ethylphenoxy)phenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol

HRID 253556Notes

Reaction equation

HRID 253556 reaction equation
[CH2:1]([C:3]1[CH:36]=[CH:35][CH:34]=[CH:33][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C@:12]([C@@H:20]1[CH2:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)([OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH3:2].[OH-].[Na+]>CC#N.Cl>[CH2:1]([C:3]1[CH:36]=[CH:35][CH:34]=[CH:33][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C@:12]([C@@H:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1)([OH:19])[CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57786507(R)-tert-butyl 3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate

Product 1

HCID 59383027(S)-1-(2-(2-ethylphenoxy)phenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (R)-tert-butyl 3-((S)-1-(2-(2-ethylphenoxy)phenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (1.50 g, 3.01 mmol) in MeCN (50 mL), 2 N aq. HCl (50 mL) was added slowly at rt. The resulting solution was stirred at room temperature overnight, then basified to pH=10 with 10 N aq NaOH aq, and MeCN was removed under vacuum. The aqueous residue was extracted with CH2Cl2 (4×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under vacuum to give (S)-1-(2-(2-ethylphenoxy)phenyl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (1.16 g, 97%) as a free amine. The crude product was used for next step without purification; MS m/z 398 (M+H+).

Workup

  1. customwas removed under vacuum
  2. extractionThe aqueous residue was extracted with CH2Cl2 (4×10 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3c4a1b7545a547fbbf251e6880f6716d
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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