HCID 68240575, compound → HCID 68240395, compound

HRID 1526416Notes

Reaction equation

HRID 1526416 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C@H:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13]3=[CH:12][C:11]=2[CH:10]=1)C1C=CC=CC=1>CCOC(C)=O>[OH:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]3[CH2:18][CH2:19][C@H:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:13]3=[CH:12][C:11]=2[CH:10]=1

Participants

3

Reactant 1

HCID 68240575HCID 68240575, compound

Product 1

HCID 68240395HCID 68240395, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-ethyl 2-(7-(benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (81.1 g, 232 mmol was dissolved in EtOAc (1.0 L) and washed w/aq. 0.5 N HCl (2×350 mL). The organics were dried over MgSO4, filtered, and concentrated to a total volume of approximately 600 mL. The solution was transferred to a Parr bottle and 10% Pd/C (22 g) was added. The mixture was placed on a Parr shaker under 50 psi of hydrogen for 3.5 h. The mixture was filtered through celite and concentrated in vacuo. The crude material was treated with hexanes:MTBE (1:1, v/v, 500 mL), and concentrated to give a white paste. The resulting paste was suspended in a mixture of hexanes:MTBE (2:1, v/v, 350 mL) and filtered. The filter cake was washed with hexanes (twice) to provide a 1st crop of (R)-ethyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate as a white solid (˜70 g, wet). Upon standing the combined filtrates contained additional precipitated product that was filtered and washed with hexanes (twice) to give a 2nd crop (˜7 g, wet) of (R)-ethyl 2-(7-hydroxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate. All remaining filtrates were concentrated and purified by silica gel chromatography (45% EtOAc in hexanes gradient to 85% EtOAc in hexanes). Concentration of the fractions containing the product provided a white solid that was filtered and washed with hexanes to give an additional 6.73 g of desired product.

Workup

  1. washwashed w/aq
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a total volume of approximately 600 mL
  5. additionwas added
  6. filtrationThe mixture was filtered through celite and
  7. concentrationconcentrated in vacuo
  8. additionThe crude material was treated with hexanes:MTBE (1:1, v/v, 500 mL)
  9. concentrationconcentrated
  10. customto give a white paste
  11. filtrationfiltered
  12. washThe filter cake was washed with hexanes (twice)

Sources & evidence

ORD record
ord-96aaf71b70934542acc308a7b6cb9dbe
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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