Ethyl Acetate → HCID 16047991, compound

HRID 888307Notes

Reaction equation

HRID 888307 reaction equation
C(OCC)(=O)C.Cl.[CH2:8]([O:15][C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([O:15][C@@H:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 16047990(3R)-3-(Benzyloxy)pyrrolidine--hydrogen chloride (1/1)

Product 1

HCID 16047991HCID 16047991, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 156 g of ethyl acetate and 100 g of water were added into 39 g of (R)-3-benzyloxypyrrolidine hydrochloride which had been obtained separately and the mixture was stirred for a while, an organic layer was separated. After 156 g of ethyl acetate was added to the resultant aqueous layer and cooled by ice, 24 g of 30% aqueous solution of sodium hydroxide was dropped. After stirring for a while and separating an aqueous layer, an organic layer was washed with 20 g of water. The resultant organic layer was concentrated and dried under reduced pressure, thereby obtaining 33 g (purity 86.6%) of a concentrate of (R)-3-benzyloxypyrrolidine. An amount of (R)-3-hydroxypyrrolidine with respect to (R)-3-benzyloxypyrrolidine was reduced from 0.84 wt % to 0.12 wt % by the above operations.

Workup

  1. customhad been obtained separately
  2. customan organic layer was separated
  3. additionAfter 156 g of ethyl acetate was added to the resultant aqueous layer
  4. temperaturecooled by ice, 24 g of 30% aqueous solution of sodium hydroxide
  5. additionwas dropped
  6. stirringAfter stirring for a while
  7. customseparating an aqueous layer
  8. washan organic layer was washed with 20 g of water
  9. concentrationThe resultant organic layer was concentrated
  10. customdried under reduced pressure
  11. customobtaining 33 g (purity 86.6%) of
  12. concentrationa concentrate of (R)-3-benzyloxypyrrolidine

Sources & evidence

ORD record
ord-1b65c1a93f15459694d8d31c8f532e71
Source dataset
uspto-grants-2012_08
Patent number
US08247578B2

Reaction notes

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