Hydrochloric Acid → HCID 67542513, compound

HRID 1809798Notes

Reaction equation

HRID 1809798 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[C@@H:10]([O:27][CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH2:9]1)=O)(C)(C)C.[ClH:39]>>[ClH:39].[CH:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:37]=[CH:38][C:29]=1[CH2:28][O:27][C@@H:10]1[C@@H:11]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

3

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67543225HCID 67543225, compound

Product 1

HCID 67542513HCID 67542513, compound

Procedure

A mixture of (3R*,4R*)-4-(3′-hydroxy-biphenyl-3-yl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid t-butyl ester (96.5 mg, 0.19 mmol) and HCl (5M in 2-propanol, 2 mL, 10 mmol) is stirred for 1 h at RT. The reaction mixture is evaporated in vacuo and the residue purified using preparative HPLC (H2O/CH3CN). The combined pure fractions are treated with solid K2CO3 and CH3CN is removed in vacuo. The aqueous layer is extracted twice with CH2Cl2. The combined organic extracts are dried (Na2SO4) and evaporated in vacuo. The residue is stirred with HCl (4M in dioxane, 1 mL, 8 mmol) for 30 min. at RT. Evaporation of the solvent affords 3′-[(3R*,4R*)-3-(naphthalen-2-ylmethoxy)-piperidin-4-yl]-biphenyl-3-ol hydrochloride as a colourless white solid: MS 410.5 [M+H]+; Rf 0.11 (DCM/MeOH 9:1).

Workup

  1. customThe reaction mixture is evaporated in vacuo
  2. customthe residue purified
  3. additionThe combined pure fractions are treated with solid K2CO3 and CH3CN
  4. customis removed in vacuo
  5. extractionThe aqueous layer is extracted twice with CH2Cl2
  6. dry with materialThe combined organic extracts are dried (Na2SO4)
  7. customevaporated in vacuo
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-38c1f9927e3c41478f4f712a62c6c31e
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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