HCID 59013462, compound → HCID 46871672, compound

HRID 1716971Notes

Reaction equation

HRID 1716971 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH2:41][CH2:40]2)C1C=CC=CC=1>CO.[Pd]>[Cl:57][C:44]1[CH:43]=[C:42]2[C:47](=[CH:46][C:45]=1[CH2:48][C:49]1[CH:50]=[CH:51][C:52]([CH2:55][CH3:56])=[CH:53][CH:54]=1)[C@:10]1([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]1)[CH2:40][CH2:41]2

Participants

4

Reactant 1

HCID 59013462HCID 59013462, compound

Product 1

HCID 46871672HCID 46871672, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran] (120 mg, 0.15 mmol) in methanol (10 mL) was added Pd/C (40 mg, 30% wt). The mixture was stirred under hydrogen (1 atm) for 12 h at room temperature. It was filtered, and the filtrate was concentrated to give a residue, which was purified by preparative HPLC to provide 52 mg (81%) of product as a white solid. 1H NMR (CD3OD, 300 MHz): δ 7.25 (s, 1H), 7.23 (s, 1H), 7.09 (m, 4H), 4.05 (s, 2H), 3.80 (m, 1H), 3.64-3.34 (m, 5H), 2.93 (dd, J=7.8, 6.6 Hz, 2H), 2.58 (q, J=7.8 Hz, 2H), 2.53 (dt, J=13.2, 7.5 Hz, 1H), 2.11 (dt, J=13.2, 7.5 Hz, 1H), 1.19 (t, J=7.8 Hz, 3H); MS ESI (m/z) 419 (M+1)+, calc. 418.

Workup

  1. filtrationIt was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give a residue, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b45629748b1a4749a84f978222655ff8
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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