Hydrochloric Acid → (3RS,4RS)-[4-[3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-phenyl}-methanol

HRID 1004989Notes

Reaction equation

HRID 1004989 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:21][CH:20]=2)[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1.Cl>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54015520tert-butyl (3RS,4RS)-3-naphthalen-2-ylmethoxy-4-(4-trityloxymethyl-phenyl)-piperidine-1-carboxylate

Product 1

HCID 69646106(3RS,4RS)-[4-[3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-phenyl}-methanolYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1.10 g (1.59 mmol) of tert-butyl (3RS,4RS)-3-naphthalen-2-ylmethoxy-4-(4-trityloxymethyl-phenyl)-piperidine-1-carboxylate in 50 ml of methanol was treated at room temperature with 30 ml of a 2M solution of hydrogen chloride in methanol and the mixture was stirred at room temperature for 4 hours. Subsequently, the solution was evaporated under reduced pressure and the residue was partitioned between 30 ml of saturated sodium carbonate solution and 50 ml of ethyl acetate. The aqueous phase was again extracted with 50 ml of ethyl acetate, thereafter the organic phases were combined, dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 90:10 mixture of methylene chloride and methanol as the eluent. There were obtained 462 mg (83% of theory) of (3RS,4RS)-[4-[3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-phenyl}-methanol as a colourless solid; MS: 348 (M+H)+.

Workup

  1. customSubsequently, the solution was evaporated under reduced pressure
  2. customthe residue was partitioned between 30 ml of saturated sodium carbonate solution and 50 ml of ethyl acetate
  3. extractionThe aqueous phase was again extracted with 50 ml of ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe crude product was chromatographed on silica gel using
  8. additiona 90:10 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-3118cf1c93974d0bb10330a788e9b347
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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