Hydrochloric Acid → (S)-2-Amino-3-[4-(4-methoxyphenoxy)-phenyl]-propan-1-ol hydrochloric acid salt

HRID 1669516Notes

Reaction equation

HRID 1669516 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.[ClH:31].O1CCOCC1>CO>[ClH:31].[NH2:8][C@@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:16][CH:15]=1)[CH2:11][OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67351484(S)-4-[4-(4-Methoxyphenoxy)-benzyl]-2,2-dimethyl-oxazolidine-3carboxylic acid tert-butyl ester

Product 1

HCID 24815980(S)-2-Amino-3-[4-(4-methoxyphenoxy)-phenyl]-propan-1-ol hydrochloric acid salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude product obtained from step 1 (100 mg, 0.25 mmol, 1 eq.) in methanol (2 ml) was added 4N HCl in dioxane (2 ml, 8 mmol, 32 eq.). The resulting mixture was stirred at room temperature for 2 hr. And then the volatile material was removed under reduced pressure. The residue thus obtained was washed with ether (3×15 ml) to remove non-acidic impurities. After dried, 75 mg of desired product (HCl salt) was obtained as white solid (99% isolated yield). 1H NMR (400 MHz, DMSO-d6) 62.87 (m, 2H), 3.27-3.30 (m, 1H), 3.36-3.41 (m, 1H), 3.50-3.55 (m, 1H), 3.93 (s, 2H), 6.91-6.95 (m, 4H), 7.19-7.30 (m, 9H), 7.93 (s, brs, 2H); LCMS (UV, ESI), 274 (M+1), 95% purity.

Workup

  1. customAnd then the volatile material was removed under reduced pressure
  2. customThe residue thus obtained
  3. washwas washed with ether (3×15 ml)
  4. customto remove non-acidic impurities
  5. customAfter dried

Sources & evidence

ORD record
ord-de46bedb85b74f3ebcd70479b12390ae
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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