Dichloromethane → (1R,2S)-3-oxo-2-pentyl-cyclopentaneacetic acid

HRID 2372Notes

Reaction equation

HRID 2372 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[C:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(Cl)Cl.C(N(CC)CC)C>CO>[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([OH:10])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 184215753-Oxo-2-pentyl-1 cyclopentene-1-acetic acid

Product 1

HCID 9920768(1R,2S)-3-oxo-2-pentyl-cyclopentaneacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a Schlenk type vessel, kept anhydrous and under Ar, there was injected the precatalytic solution (6.75 ml) containing 47 mg (0.05 mmole) of bis(trifluoro-acetato)[(+)-(R)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl]ruthenium (II), 3-oxo-2-pentyl-1-cyclopentene-1-acetic acid (0.5 g, 2.4 mmole), CH2Cl2 (5 ml), methanol (5 ml) and triethylamine (10.28 mg, 0.1 mmole, 14 μl, dist. over KOH). After stirring for 5 min, the orange soltion was filtered through a single use filter (Acrodisc 0.45 μm) in a dry autoclave (100 ml/107Pa) under Ar. The autoclave was then connected to a source of hydrogen and rinsed 5× with hydrogen at a pressure of 106Pa. The autoclave was then pressurized at 9×106Pa. Stirring at this pressure and 25° was carried out during 120 h. Afterwards, the pressure was gently released, the autoclave opened and the orange solution concentrated.

Workup

  1. customInto a Schlenk type vessel, kept anhydrous and under Ar, there
  2. filtrationthe orange soltion was filtered through a single use
  3. filtrationfilter (Acrodisc 0.45 μm) in a dry autoclave (100 ml/107Pa) under Ar
  4. washrinsed 5× with hydrogen at a pressure of 106Pa
  5. stirringStirring at this pressure and 25°
  6. waitwas carried out during 120 h
  7. concentrationthe orange solution concentrated

Sources & evidence

ORD record
ord-a0652456c8c14b52877012b598e65bcc
Source dataset
uspto-grants-1998_03
Patent number
US05728866

Reaction notes

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