Methanol → HCID 86640055, compound

HRID 2427284Notes

Reaction equation

HRID 2427284 reaction equation
[CH:1]([O:4][C:5](=[O:28])[NH:6][C@@H:7]1[CH2:27][C:10]2[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:12]3[CH:13]=[CH:14][C:15]([C:18]#N)=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:3])[CH3:2].C[OH:30]>C(O)=O.O.[Ni].[Al]>[CH:1]([O:4][C:5](=[O:28])[NH:6][C@@H:7]1[CH2:27][C:10]2[N:11]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:12]3[CH:13]=[CH:14][C:15]([CH:18]=[O:30])=[CH:16][C:17]=3[C:9]=2[CH2:8]1)([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 887MethanolHCID 24963749LY-2452473

Product 1

HCID 86640055HCID 86640055, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 6336846Nickel aluminideCatalystHCID 284Formic AcidSolventHCID 962WaterSolvent2×

Procedure

Dissolve (S)-(7-cyano-4-pyridin-2-ylmethyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (200 mg, 0.53 mmol) in 88% formic acid (10 ml) and water (1 mL). Add aluminum-nickel catalyst (50/50 wt %) and heat at 90° C. for 24 h. Add water (1 mL) and heat for an additional 24 h. After cooling to room temperature, add methanol and filter off the catalyst through Celite®. Dilute with ethyl acetate and basify to pH=10 using 10% potassium carbonate. Separate the phases and wash the organic phase with 10% potassium carbonate. Dry the organic portion over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound as an orange oil (181 mg, 91%). Use the crude product without further manipulation. MS (m/z): 378.2 (M+1).

Workup

  1. filtrationfilter off the catalyst through Celite®
  2. additionDilute with ethyl acetate
  3. customSeparate the phases
  4. washwash the organic phase with 10% potassium carbonate
  5. dry with materialDry the organic portion over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-a4a345f8bc344eb6ad35c35a415f779a
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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