Methane → HCID 69595584, compound

HRID 356534Notes

Reaction equation

HRID 356534 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C@:17]2([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[O:22][C:21](=[O:23])[CH:20]=[C:19]([OH:24])[CH2:18]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.C>[Pd].C1COCC1>[CH:25]1([C@@:17]2([CH2:16][CH2:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=3)[O:22][C:21](=[O:23])[CH:20]=[C:19]([OH:24])[CH2:18]2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 297MethaneHCID 70254340HCID 70254340, compound

Product 1

HCID 69595584HCID 69595584, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 4 using (S)-6-[2-(3-benzyloxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one (0.64 g, 1.63 mmol) from Example EEEEE, 0.1 g of 20% Pd over charcoal and THF (16 mL). Purification by silica gel chromatography, eluting with CH2Cl2 :MeOH (97.5:2.5) gave the title compound. 1H-NMR (DMSO-d6) δ 1.3-1.7 (m, 8 H), 1.85-1.95 (m, 2 H), 2.35 (t, 1 H), 2.4-2.6 (m, 4 H), 4.95 (s, 1 H), 6.55-6.6 (m, 3 H), 7.05 (t, 1 H), 9.25 (s, 1 H), 11.35 (s, 1 H).

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography
  3. washeluting with CH2Cl2 :MeOH (97.5:2.5)

Sources & evidence

ORD record
ord-4b5649e324b84f4bbb5c4868c732e8ea
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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