HCID 86687113, compound → HCID 86687114, compound

HRID 630832Notes

Reaction equation

HRID 630832 reaction equation
[CH3:1][O:2][C:3]([C@:5]1([CH2:11][O:12]CC2C=CC=CC=2)[CH2:9][CH2:8][CH2:7][N:6]1[CH3:10])=[O:4]>[OH-].[OH-].[Pd+2].C(O)(=O)C>[CH3:1][O:2][C:3]([C@:5]1([CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][N:6]1[CH3:10])=[O:4]

Participants

4

Reactant 1

HCID 86687113HCID 86687113, compound

Product 1

HCID 86687114HCID 86687114, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of Intermediate 85d (2.59 g, 9.84 mmol), palladium hydroxide on charcoal (10%, 250 mg) and glacial acetic acid (1 mL) in IMS (20 mL) under an atmosphere of hydrogen (1 atm) was stirred at RT for 5 d. The mixture was filtered and concentrated in vacuo to give the title compound as a clear oil (1.70 g, 99%), as a mixture of methyl and ethyl esters. Data for major product, methyl ester: 1H NMR (400 MHz, CDCl3): 1.75-1.95 (2H, m), 2.01-2.18 (2H, m), 2.36 (3H, s), 2.86-2.99 (2H, m), 3.65 (3H, s), 4.19 (2H, m), 4.91 (1H, br s).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fce868d1e76c4cc7808c13cc2880ff72
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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