Ammonium Chloride → HCID 9905364, compound

HRID 1719883Notes

Reaction equation

HRID 1719883 reaction equation
[BH4-].[Na+].[CH2:3]([C@H:11]1[CH2:15][CH2:14][C@@H:13]([C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[NH:12]1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+]>C(O)C>[CH2:3]([CH:11]1[CH2:15][CH2:14][CH:13]([CH:16]([OH:26])[C:17]2[CH:22]=[CH:21][C:20]3[O:23][CH2:24][O:25][C:19]=3[CH:18]=2)[NH:12]1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86740340HCID 86740340, compound

Product 1

HCID 9905364HCID 9905364, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.35 g (0.035 mole) of sodium borohydride was added to a stirred solution of 2.70 g (0.0057 mole) of ±cis 2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrolidine in 270 ml ethanol, at 0° temperature. After 1 hour at 0°, the mixture was poured into 100 ml of 10% ammonium chloride solution. The mixture was evaporated in vacuo to remove the ethanol, the residue was cooled to 0°, and 50 ml of a saturated sodium carbonate solution was added. The product was extracted into ethyl acetate, the extract was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate-hexane to give 1.72 g (93%) of the desired ±cis erythro 2-[phenethyl]-5-[(3,4-methylenedioxy)-α-hydroxybenzyl]pyrrolidine (IX), m.p. 122°-123° (dichloromethane-hexane). (Step 7)

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto remove the ethanol
  3. temperaturethe residue was cooled to 0°
  4. addition50 ml of a saturated sodium carbonate solution was added
  5. extractionThe product was extracted into ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6d3d474953f3439486e1d883be9b37f6
Source dataset
uspto-grants-1985_09
Patent number
US04543361

Reaction notes

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