HCID 2475880, compound → HCID 69722213, compound

HRID 2307665Notes

Reaction equation

HRID 2307665 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C@@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][NH:13][C@@H:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 2475880HCID 2475880, compound

Product 1

HCID 69722213HCID 69722213, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 52A (2.07 g) in THF (20 mL) was treated with borane-tetrahydrofuran complex (12 mL, 12 mmol) and heated at reflux for 1.5 hours. The mixture was allowed to cool to room temperature and quenched with 1N NaOH. The mixture was stirred 30 for minutes and diluted with diethyl ether. The separated organic phase was washed with brine, dried (Na2SO4), filtered and the filtrate concentrated. The residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexanes) to provide the title compound as a pale brown oil (0.48 g, 28% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. customquenched with 1N NaOH
  4. additiondiluted with diethyl ether
  5. washThe separated organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated
  9. customThe residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d9e1dd2afbb4486ebd1ba697081b6ba4
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

Loading…