HCID 25028926, compound → HCID 59293944, compound

HRID 1644779Notes

Reaction equation

HRID 1644779 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22]3)[C@@H:18]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>Cl.O1CCOCC1>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]([O:16][C@H:17]2[CH2:25][CH2:24][C@H:23]3[C@@H:19]([CH2:20][NH:21][CH2:22]3)[C@@H:18]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:14][OH:15])[CH:4]=[C:3]([C:2]([F:41])([F:40])[F:1])[CH:8]=1

Participants

4

Reactant 1

HCID 25028926HCID 25028926, compound

Product 1

HCID 59293944HCID 59293944, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The more polar isomer (1S) isomer of EXAMPLE 1 (tert-butyl (3aR,4R,5S,7aS)-5-{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyethoxy}-4-(2-methylphenyl)octahydro-2H-isoindole-2-carboxylate, 2.0 g, 3.4 mmol) was stirred in 4 N HCl in dioxane for 1 hr. The volatiles were removed, and the residue was taken into ethyl acetate. The organic layer was separated, and the aqueous was extracted with ethyl acetate. The combined organic layers were washed consecutively with 2 N NaOH, brine, dried over MgSO4 and the solvent was removed to give 1.65 g of the amine title compound. M++1: 488.22

Workup

  1. customThe volatiles were removed
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted with ethyl acetate
  4. washThe combined organic layers were washed consecutively with 2 N NaOH, brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-95277a320e2047eb96fd4022f9110a9f
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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