Methanol → (3aR,4S,-5R,6aS)-4-acetylhexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

HRID 1607740Notes

Reaction equation

HRID 1607740 reaction equation
[Na].[CH3:2][CH:3]1[CH2:11][CH:6]2[O:7][C:8](=[O:10])[CH2:9][CH:5]2[CH2:4]1.[N+](=[CH2:15])([O-])[O-].S(=O)(=O)(O)O.[CH3:21][OH:22]>O.C(O)(=O)C>[C:21]([C@@H:4]1[C@@H:5]2[C@@H:6]([O:7][C:8](=[O:10])[CH2:9]2)[CH2:11][C@H:3]1[CH3:2])(=[O:22])[CH3:15]

Participants

8

Reactant 5

HCID 887Methanol3×HCID 1118Sulfuric AcidHCID 5360545SodiumHCID 12383287hexahydro-5-methyl-2H-cyclopenta[b]furan-2-oneHCID 178486260Methanenitronate

Product 1

HCID 13560255(3aR,4S,-5R,6aS)-4-acetylhexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium (1.3 g) was dissolved in methanol (30 mL) and the solution added at 0° to a methanol (40 mL) solution of the crude, optically active (3aR,4S,5R,6aS)-4-nitroethyl)hexahydro-5-methyl-2H-cyclopenta[b]-furan-2-one (10.0 g). This nitronate anion solution was added, 30 minutes later and at -30°, to a cold (-30° ) solution of concentrated sulfuric acid (6 mL) in methanol (40 mL). The resulting mixture was processed as in example III, including hydrolysis with acetic acid (8 mL) in water (30 mL) while stripping, to give 8.47 g (99%) of the crude, optically active (3aR,4S,-5R,6aS)-4-acetylhexahydro-5-methyl-2H-cyclopenta[b]furan-2-one as a yellow oil. This material was used directly in Example XIV.

Workup

  1. customat -30°

Sources & evidence

ORD record
ord-9bf282b0e0d746a3b802610fb941a0fc
Source dataset
uspto-grants-1989_09
Patent number
US04866205

Reaction notes

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