Sodium Hydroxide → (S)-1-(benzo[b]thiophen-2-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol

HRID 2355375Notes

Reaction equation

HRID 2355375 reaction equation
[S:1]1[C:5]([C@:6]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)([OH:13])[CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]2[CH:27]=[CH:28][CH:29]=[CH:30][C:2]1=2.[OH-].[Na+]>Cl.C(#N)C>[S:1]1[C:5]([C@:6]([C@@H:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)([OH:13])[CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]2[CH:27]=[CH:28][CH:29]=[CH:30][C:2]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59382892(R)-tert-butyl 3-((S)-1-(benzo[b]thiophen-2-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate

Product 1

HCID 59382913(S)-1-(benzo[b]thiophen-2-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

(R)-tert-butyl 3-((S)-1-(benzo[b]thiophen-2-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (160 mg, 0.37 mmol) was dissolved in 1:1 2 N aq HCl solution/acetonitrile (50 mL). The mixture was stirred overnight at rt and neutralized with 5% aq NaOH. The acetonitrile was removed by evaporation. The aqueous residue was extracted by CH2Cl2 (2×40 mL). The combined organic layers were concentrated to afford (S)-1-(benzo[b]thiophen-2-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (102 mg, 83%) which was used without purification.

Workup

  1. customThe acetonitrile was removed by evaporation
  2. extractionThe aqueous residue was extracted by CH2Cl2 (2×40 mL)
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-708b5ba19cb442999d21975066b74357
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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