Sodium Sulfate → HCID 71227035, compound

HRID 2370002Notes

Reaction equation

HRID 2370002 reaction equation
O=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.[C@@H:18]1([NH2:25])[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[NH2:24].[O-]S([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.C(Cl)Cl>[NH2:24][C@@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]1[NH:25][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 438061,2-Diaminocyclohexane, trans-HCID 5049666Sodium triacetoxyborohydrideHCID 10105382HCID 10105382, compound

Product 1

HCID 71227035HCID 71227035, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask under argon was added the ethyl 4-(3-oxopyrrolidin-1-yl)benzoate (1.23 g, 5.27 mmol), (1R,2R)-cyclohexane-1,2-diamine (0.602 g, 5.27 mmol), CH2Cl2 (30 ml), solid anhydrous Na2SO4 (2.5 gm) and HOAc (1 ml). Argon was bubbled through the reaction mixture for 1 min and then the reaction was stirred under argon at rt for 1 hr. After this time, sodium triacetoxy borohydride (2.012 g, 9.49 mmol) was added to the reaction which was then stirred at rt overnight. The reaction was filtered and water (10 ml) was added to the reaction. The reaction mixture was then diluted with CH2Cl2 (100 ml). The resulting solution was washed with saturated aqueous NaHCO3 (100 ml), water (50 ml) and saturated aqueous NaCl (50 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated to give the product ethyl 4-(3-((1R,2R)-2-aminocyclohexylamino)pyrrolidin-1-yl)benzoate (1 g, 3.02 mmol, 57.2% yield) as brown solid. Anal. Calcd. for C19H29N3O2 m/z 331.4, found: 332.1 (M+H)+.

Workup

  1. customArgon was bubbled through the reaction mixture for 1 min
  2. stirringwas then stirred at rt overnight
  3. filtrationThe reaction was filtered
  4. additionwater (10 ml) was added to the reaction
  5. additionThe reaction mixture was then diluted with CH2Cl2 (100 ml)
  6. washThe resulting solution was washed with saturated aqueous NaHCO3 (100 ml), water (50 ml) and saturated aqueous NaCl (50 ml)
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7c1608c4594f4632a7e6170c99ce389a
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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