HCID 66654037, compound → HCID 89524127, compound

HRID 2036221Notes

Reaction equation

HRID 2036221 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:18])[CH:14]=2)[C@H:9]1[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=O)(C)(C)C>CCO.Cl.O1CCOCC1>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][O:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[C@@H:9]1[C:10]2[C:15](=[CH:14][C:13]([F:18])=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1)[CH3:32]

Participants

5

Reactant 1

HCID 66654037HCID 66654037, compound

Product 1

HCID 89524127HCID 89524127, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice-cooled solution of (S)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-6-fluoro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (640 mg, 1.38 mmol, 1 eq.) in EtOH (2.5 mL), 4M HCl in dioxane (5.5 mL) was added. The resulting solution was stirred at r.t. for 3 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between AcOEt and a sat. aq. NaHCO3 soln. The layers were separated and the aq. phase was extracted with AcOEt. The comb. org. phases were concentrated in vacuo to give the free amine.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between AcOEt
  4. customThe layers were separated
  5. extractionthe aq. phase was extracted with AcOEt
  6. concentrationphases were concentrated in vacuo

Sources & evidence

ORD record
ord-d60cd797b44c4aa6b3fe183167a6f83a
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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