HCID 67216429, compound → HCID 58557162, compound

HRID 1969567Notes

Reaction equation

HRID 1969567 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][C:5](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4]1)[CH3:2]>C(Cl)Cl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CC=CCCC=C1.C1C=CN=CC=1.F[P-](F)(F)(F)(F)F.[Ir]>[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][C@H:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 67216429HCID 67216429, compound

Product 1

HCID 58557162HCID 58557162, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 5702647(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-((3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentylidene)acetate (0.160 g, 0.754 mmol) in DCM (3 mL) was added Crabtree's catalyst (0.030 g, 0.038 mmol). The reaction mixture was sparged with hydrogen for about 5 min and an atmosphere of hydrogen was maintained via balloon. After about 24 h, the reaction mixture was concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (30-80%) to provide ethyl 2-((1R,3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentyl)acetate (0.140 g, 87%) as an oil. 1H NMR (400 MHz, CDCl3) δ 4.12 (q, J=7.1 Hz, 2H), 3.71-3.64 (dd, J=10.5, 8.0 Hz, 1H), 3.47 (dd, J=10.5, 8.0 Hz, 1H), 2.55-2.41 (m, 1H), 2.32 (d, J=6.7 Hz, 2H), 2.02-1.89 (m, 1H), 1.88-1.76 (m, 1H), 1.70-1.60 (m, 1H), 1.48-1.33 (m, 4H), 1.26 (t, J=7.1 Hz, 3H), 1.22-1.07 (m, 1H), 0.90 (t, J=7.4 Hz, 3H).

Workup

  1. customThe reaction mixture was sparged with hydrogen for about 5 min
  2. temperaturean atmosphere of hydrogen was maintained via balloon
  3. custompurified by chromatography on silica gel eluting with EtOAc/heptane (30-80%)

Sources & evidence

ORD record
ord-69bcce920e9c47e2ae83bdae1058db5d
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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