Hydrochloric Acid → HCID 12804793, compound

HRID 1648919Notes

Reaction equation

HRID 1648919 reaction equation
B.[CH:2]1([C:5]([N:7]2[CH2:11][CH2:10][C:9]([OH:25])([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:8]2)=O)[CH2:4][CH2:3]1.[ClH:26].Cl.CCOCC>C1COCC1>[ClH:26].[CH:2]1([CH2:5][N:7]2[CH2:11][CH2:10][C:9]([OH:25])([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:8]2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 10953452Ether hydrochlorideHCID 13288029HCID 13288029, compound

Product 1

HCID 12804793HCID 12804793, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 45 ml of 1 M-borane in THF is added under dry nitrogen at 0° C., 6.36 g 1-cyclopropylcarbonyl-3-hydroxy-3-(α-phenyl-2-tolyl)pyrrolidine in 20 ml of dry THF. The solution is then brought to reflux and maintained there for 1 hour. The solution is permitted to cool to room temperature and 3.3 ml of 6 N-HCl is added slowly. The THF is removed by distillation at atmospheric pressure and the residue is crystallized with 50 ml of anhydrous ether and recrystallized from methanol/ether (30 ml/80 ml) to give colorless crystals. The mother liquid is made acid with a slight excess of HCl/ether and a second crop is obtained by suction filtration. The mother liquid is concentrated in vacuo to an oil and a third crop is obtained by crystallization with ether. Recrystallization from methanol/ether (20 ml/50 ml) yields 1-cyclopropylmethyl-3-hydroxy-3-(α-phenyl-2-tolyl)pyrrolidine hydrochloride, mp 168°-169° C.

Workup

  1. temperatureto reflux
  2. temperaturemaintained there for 1 hour
  3. customThe THF is removed by distillation at atmospheric pressure
  4. customthe residue is crystallized with 50 ml of anhydrous ether
  5. customrecrystallized from methanol/ether (30 ml/80 ml)
  6. customto give colorless crystals
  7. customa second crop is obtained by suction filtration
  8. concentrationThe mother liquid is concentrated in vacuo to an oil
  9. customa third crop is obtained by crystallization with ether
  10. customRecrystallization from methanol/ether (20 ml/50 ml)

Sources & evidence

ORD record
ord-8fb0fb42de3f46a38f40692d2725594a
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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