Hydrochloric Acid → Ethyl 4-(Benzo[d][1,3]dioxol-5-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylate

HRID 1272534Notes

Reaction equation

HRID 1272534 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]([C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[CH2:11][N:10]=2)=[CH:5][CH:4]=1.C([BH3-])#N.[Na+].Cl>CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]([C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[CH2:11][NH:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 105951072PC69SX5ZB

Product 1

HCID 10785314Ethyl 4-(Benzo[d][1,3]dioxol-5-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylateYield 96.8%

Reagents, catalysts & solvents 2

HCID 6451Bromocresol GreenCatalystHCID 702EthanolSolvent

Procedure

Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet was charged 0.460 kg ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4,5-dihydro-3H-pyrrole-3-carboxylate (1.25 mol). The reaction vessel was degassed with nitrogen. Absolute 3.7 L ethanol and 1.12 L of THF were added. 31 mg bromocresol green and 94.26 g sodium cyanoborohydride (1.5 mol) were added. A solution containing 400 mL absolute ethanol and 200 mL of 12 M HCl was then added. The reaction mixture was stirred for 30 minutes after addition was complete. After the starting material was consumed, 0.5 L of 7% aq. NaHCO3 was added. The reaction mixture was concentrated and diluted with 5 L ethyl acetate. The organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl, the dried over 190 g MgSO4, filtered, and concentrated to give 447 g of the title compound as a thick yellow oil.

Workup

  1. customInto a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet
  2. customThe reaction vessel was degassed with nitrogen
  3. additionAbsolute 3.7 L ethanol and 1.12 L of THF were added
  4. additionwas then added
  5. additionafter addition
  6. customAfter the starting material was consumed
  7. addition0.5 L of 7% aq. NaHCO3 was added
  8. concentrationThe reaction mixture was concentrated
  9. additiondiluted with 5 L ethyl acetate
  10. washThe organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl
  11. dry with materialthe dried over 190 g MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-f7a2457c192b474caf729d8d376212c2
Source dataset
uspto-grants-2007_04
Patent number
US07208517B1

Reaction notes

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