Tetrahydrofuran → HCID 67917369, compound

HRID 892810Notes

Reaction equation

HRID 892810 reaction equation
C([O:4][C@:5]1(O)[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:15])[CH:11]=2)[C@:6]1([C:19](C)([CH3:21])[CH3:20])C(C)C)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O:32]1CC[CH2:34][CH2:33]1>>[F:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[C@@H:6]([CH:19]([CH3:20])[CH3:21])[C@@:5]([CH2:34][CH2:33][OH:32])([OH:4])[CH2:14][CH2:13]2

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67917383HCID 67917383, compound

Product 1

HCID 67917369HCID 67917369, compound

Procedure

A solution of 82.2 g (0.255 mol) of [1R,2R]-(-)-t-butyl-6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl acetate in 500 ml of abs. tetrahydrofuran was added within 30 minutes to a cooled suspension of 19.4 g (0.51 mol) of lithium aluminum hydride in 500 ml of abs. tetrahydrofuran in such a manner that the temperature did not exceed 30°. After stirring for a further 30 minutes the reaction mixture was cooled to 5° and carefully treated in succession with 30 ml of ice-water, 30 ml of 1N sodium hydroxide solution and 90 ml of ice-water. Thereafter, the mixture was stirred for a further 60 minutes and filtered, and the filtrate evaporated under reduced pressure. The oily residue was dissolved in a 20:1 mixture of chloroform and methanol and chromatographed on 900 g of silica gel, yielding [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethanol as white crystals, m.p. 78°-80°; [α]D20 =-83.1° (c=1, methanol).

Workup

  1. customdid not exceed 30°
  2. temperaturewas cooled to 5°
  3. stirringThereafter, the mixture was stirred for a further 60 minutes
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure
  6. dissolutionThe oily residue was dissolved in a 20:1 mixture of chloroform and methanol
  7. customchromatographed on 900 g of silica gel

Sources & evidence

ORD record
ord-55a096d441f541b280900bfd9907dea5
Source dataset
uspto-grants-1992_06
Patent number
US05120759

Reaction notes

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