HCID 86614034, compound → HCID 10076562, compound

HRID 1727163Notes

Reaction equation

HRID 1727163 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@H:23]([C@H:24]([C:31]([CH3:33])=[CH2:32])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:34])[C@H:20]4[O:35][C:36](=[O:38])[CH3:37])=[O:17])[CH2:15][C@@:7]3([OH:39])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)(C)C.[Pt]>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][C@@H:19]4[C@:28]5([OH:29])[C@@H:23]([C@H:24]([CH:31]([CH3:32])[CH3:33])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:34])[C@H:20]4[O:35][C:36](=[O:38])[CH3:37])=[O:17])[CH2:15][C@@:7]3([OH:39])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86614034HCID 86614034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10076562HCID 10076562, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of (1S,2R,4aS,5R,8R,8aR)-2-(acetyloxy)-8a-hydroxy-3,8-dimethyl-5-(1-methylethenyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b -hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 1,200 mg) in isopropanol (20 ml) was added platinum on carbon (10% w/w, 20 mg) and the resulting mixture was hydrogenated at room temperature with stirring under 1 atmosphere pressure of hydrogen for 18 hours. The mixture was filtered through celite and concentrated in vacuo to give a white solid. The solid was purified by preparative HPLC (1 inch diameter Ultrasphere C18 column, 2 injections; 70:30 acetonitrile:water) to give the product as a white solid (89 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated in vacuo
  4. customto give a white solid
  5. customThe solid was purified by preparative HPLC (1 inch diameter Ultrasphere C18 column, 2 injections

Sources & evidence

ORD record
ord-4fd790d2dff9449c81a133953de7317f
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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