Ethanol hydrochloride → HCID 67422867, compound

HRID 1920801Notes

Reaction equation

HRID 1920801 reaction equation
[ClH:1].C(O)C.C([O:12][C@H:13]1[CH2:17][NH:16][C@H:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([F:26])[CH:20]=2)[CH2:14]1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].[C].CO>[ClH:1].[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[CH3:25])[CH2:18][C@H:15]1[NH:16][CH2:17][C@H:13]([OH:12])[CH2:14]1

Participants

5

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 58581013HCID 58581013, compound

Product 1

HCID 67422867HCID 67422867, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 887MethanolSolvent

Procedure

By adding 2 M hydrochloric acid/ethanol solution (15 mL) to (2R,4R)-4-(benzyloxy)-2-(3-fluoro-4-methylbenzyl)pyrrolidine (1.45 g, 4.84 mmol) which had been synthesized according to Example 1 (1e)-20, a suspension was prepared. Methanol (10 mL) was added thereto to yield a homogenous solution. 20% Palladium hydroxide-carbon (wet, 50 wt %, 483 mg) was added thereto for hydrogenation under atmospheric pressure for 16 hours. The reaction solution was filtered. The solvent was distilled off under reduced pressure. The residue was added with diethyl ether to yield a suspension, which was then filtered and washed with diethyl acetate to give the title compound as a white solid (1.13 g, yield 95%).

Workup

  1. customhad been synthesized
  2. customa suspension was prepared
  3. customto yield a homogenous solution
  4. filtrationThe reaction solution was filtered
  5. distillationThe solvent was distilled off under reduced pressure
  6. additionThe residue was added with diethyl ether
  7. customto yield a suspension, which
  8. filtrationwas then filtered
  9. washwashed with diethyl acetate

Sources & evidence

ORD record
ord-c7dcb2ede8e04183bacdb531bd16a0ff
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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