Acetic Acid → HCID 68180905, compound

HRID 538676Notes

Reaction equation

HRID 538676 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH:14]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1.C(O)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][CH2:14][NH:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 763102-AminoindaneHCID 21851991tert-Butyl 2-(2-oxoethyl)pyrrolidine-1-carboxylate

Product 1

HCID 68180905HCID 68180905, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound 38 (2.3 g, 10.80 mmol) in DCM (90 mL) were added successively 2-aminoindane (1.4 mL, 10.80 mmol), Na(OAC)3BH (6.86 g, 32.39 mmol) and acetic acid (2 mL) at 0° C. The resulting mixture was allowed to stir at rt for 16 hours. The reaction mixture was diluted in DCM and washed with 1N NaOH, water and brine solution. The organic layer was dried over anhydrous Na2SO4, filtered and evaporated. The crude material was purified by Combiflash® chromatography eluting with 3-4% of methanol-DCM to provide compound 39.

Workup

  1. washwashed with 1N NaOH, water and brine solution
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by Combiflash® chromatography
  6. washeluting with 3-4% of methanol-DCM

Sources & evidence

ORD record
ord-97d109490d6e43f98336056fdc9c4a6c
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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