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

HRID 3008

Reaction equation

HRID 3008 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 12M 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-cc2851f5ea1a4929ac56dab75ef1b205
Source dataset
uspto-grants-1998_03
Patent number
US05731434

Linked notes

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