Tetrahydrofuran → HCID 20801253, compound

HRID 1071580Notes

Reaction equation

HRID 1071580 reaction equation
C(OC([C@]1(C)CCCN([CH2:12][C@H:13]2[C@H:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:17]([O:25][C@@H:26]([C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=3)[CH3:27])[CH2:16][O:15][CH2:14]2)C1)=O)C.[O:43]1CCCC1>>[F:39][C:38]([F:40])([F:41])[C:30]1[CH:29]=[C:28]([C@H:26]([O:25][C@H:17]2[CH2:16][O:15][CH2:14][CH:13]([CH2:12][OH:43])[C@@H:18]2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:27])[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 86759762HCID 86759762, compound

Product 1

HCID 20801253HCID 20801253, compound

Procedure

A solution of borane-tetrahydrofuran complex in tetrahydrofuran (1M, 25 ml) was added dropwise to a stirred, ice-bath cooled solution of the product from Description 44 (5.8 g, 13.5 mmol) in tetrahydrofuran (70 ml). The cold-bath was removed and the mixture was stirred at ambient temperature. After 30 minutes, the mixture was cooled to 0° C. and carefully treated with 2M aqueous NaOH (20 ml) and 35% hydrogen peroxide (20 ml). The cold bath was removed and the mixture was stirred for 1 hour. After cooling to 0°, the reaction was carefully treated with 25% aqueous solution of Na2S3O5 (125 ml) and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on silica (i-hexane:ethyl acetate) to give a mixture of diastereoisomeric alcohols (5.34 g) in the ratio (3S):(3R)=1.9:1.

Workup

  1. customThe cold-bath was removed
  2. temperaturethe mixture was cooled to 0° C.
  3. additioncarefully treated with 2M aqueous NaOH (20 ml) and 35% hydrogen peroxide (20 ml)
  4. customThe cold bath was removed
  5. stirringthe mixture was stirred for 1 hour
  6. temperatureAfter cooling to 0°
  7. additionthe reaction was carefully treated with 25% aqueous solution of Na2S3O5 (125 ml)
  8. extractionextracted into ethyl acetate
  9. dry with materialThe combined organic extracts were dried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by chromatography on silica (i-hexane:ethyl acetate)
  12. customto give

Sources & evidence

ORD record
ord-b489b8f21b7d46c3a1ba9b6e3969a362
Source dataset
uspto-grants-2005_06
Patent number
US06906085B2

Reaction notes

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