Acetic Acid → Pyrrolidine, 1-(2,3-dihydro-1H-inden-2-yl)- (9CI)

HRID 710595Notes

Reaction equation

HRID 710595 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 206203Pyrrolidine, 1-(2,3-dihydro-1H-inden-2-yl)- (9CI)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1H-inden-2(3H)-one (6 g, 45.4 mmol) in 100 mL of methanol were added pyrrolidine (7.51 ml, 91 mmol), sodium cyanoborohydride (5.71 g, 91 mmol), and acetic acid (5.20 ml, 91 mmol). The reaction mixture was stirred overnight then concentrated. The crude residue was dissolved in 400 mL of ethyl acetate and washed with aqueous sodium bicarbonate (2×400 mL) and saturated aqueous brine (1×200 mL), dried over magnesium sulfate, filtered and concentrated. Recrystallization in ethyl acetate/hexane afforded the title compound. MS (ESI) m/z 188 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe crude residue was dissolved in 400 mL of ethyl acetate
  3. washwashed with aqueous sodium bicarbonate (2×400 mL) and saturated aqueous brine (1×200 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallization in ethyl acetate/hexane

Sources & evidence

ORD record
ord-65d7e892b0d041c79bc3714285af1698
Source dataset
uspto-grants-2015_11
Patent number
US09181239B2

Reaction notes

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