Tetrahydrofuran → HCID 14988545, compound

HRID 981767Notes

Reaction equation

HRID 981767 reaction equation
[CH2:1]([O:8][N:9]1[CH:12]([C:13](OCC2C=CC=CC=2)=[O:14])[CH2:11][C:10]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[BH4-].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[CH2:1]([O:8][N:9]1[CH:12]([CH2:13][OH:14])[CH2:11][C:10]1=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 20070740HCID 20070740, compound

Product 1

HCID 14988545HCID 14988545, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 311 mg. (1 mmole) of 1-benzyloxy-4-benzyloxycarbonylazetidin-2-one in 10 ml. of tetrahydrofuran, cooled in an ice bath, was added a solution of 37 mg. of sodium borohydride in 3 ml. of water. The solution was stirred at ice bath temperature for one hour and was then poured into a separatory funnel containing 25 ml. of ethyl acetate, 25 ml. of water and 2 ml. of acetic acid. After shaking, the layers were separated and the aqueous layer was extracted twice with 25 ml. portions of ethyl acetate. These two extracts were combined with the organic layer. The organic layer was washed twice with 15 ml. portions of 5% aqueous sodium bicarbonate and 15 ml. of brine and was dried over sodium sulfate, filtered and evaporated to give the product as a crude oil. The oil was chromatographed on silica gel with gradient elution (30% ethyl acetate -70% hexanes to 100% ethyl acetate) The fraction containing the purified product (Rf=0.15, silica gel thin layer in 1:1 ethyl acetate-hexanes) was evaporated to yield 121 mg. (61% yield) of the product as an oil.

Workup

  1. additionwas added a solution of 37 mg
  2. additionwas then poured into a separatory funnel
  3. additioncontaining 25 ml
  4. stirringAfter shaking
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted twice with 25 ml
  7. washThe organic layer was washed twice with 15 ml
  8. dry with materialof brine and was dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto give the product as a crude oil
  12. customThe oil was chromatographed on silica gel with gradient elution (30% ethyl acetate -70% hexanes to 100% ethyl acetate) The fraction
  13. additioncontaining the purified product (Rf=0.15, silica gel thin layer in 1:1 ethyl acetate-hexanes)
  14. customwas evaporated
  15. customto yield 121 mg

Sources & evidence

ORD record
ord-d27d44dca07f4f8f9daf117683fae527
Source dataset
uspto-grants-1991_02
Patent number
US04992544

Reaction notes

Loading…