Reaction #1121757

ord-f658e7d46e484d3baf7ff1bac8d4308c

Reaction equation

CC(=O)O[C@H]1C=C(CC(=O)OCc2ccccc2)C(=O)C1
(R)-2-benzoxycarbonylmethyl-4-acetyloxy-2-cyclopenten-1-one
OCc1ccccc1
benzyl alcohol
CCOC(=O)CC1=C[C@H](OC(C)=O)CC1=O
(R)-2-ethoxycarbonylmethyl-4-acetoxy-2-cyclopenten-1-one
→
O=C(CC1=C[C@H](O)CC1=O)OCc1ccccc1
titled compound
O=C(CC1=C[C@H](O)CC1=O)OCc1ccccc1
(R)-2-benzoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one

Reactants

CC(=O)O[C@H]1C=C(CC(=O)OCc2ccccc2)C(=O)C1
(R)-2-benzoxycarbonylmethyl-4-acetyloxy-2-cyclopenten-1-one
OCc1ccccc1
benzyl alcohol
CCOC(=O)CC1=C[C@H](OC(C)=O)CC1=O
(R)-2-ethoxycarbonylmethyl-4-acetoxy-2-cyclopenten-1-one

Reagents

None

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Example 34: Example 34 was conducted according the procedure of Example 32 except that the starting material was (R)-2-benzoxycarbonylmethyl-4-acetyloxy-2-cyclopenten-1-one (4 g, 97% e.e.) and benzyl alcohol were used instead of (R)-2-ethoxycarbonylmethyl-4-acetoxy-2-cyclopenten-1-one and ethanol. The titled compound was obtained with high optical purity (3.4 g, 99% e.e.).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08546114B2uspto-grants-2013_10