Ethanol → HCID 66797936, compound

HRID 1747647Notes

Reaction equation

HRID 1747647 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@@H:6]1[NH:14]C(=O)OC(C)(C)C)=[O:4].C(O)C>C(Cl)Cl.[Br-].[Br-].[Zn+2]>[NH2:14][C@H:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C@H:5]1[C:3]([N:2]([CH3:22])[CH3:1])=[O:4]

Participants

5

Reactant 2

HCID 702EthanolHCID 66797899HCID 66797899, compound

Product 1

HCID 66797936HCID 66797936, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl rel-{(1R,2R)-2-[(dimethylamino)carbonyl]-2,3-dihydro-1H-inden-1-yl}carbamate (690 mg, 2.15 mmol) in DCM (25.0 mL) was added zinc dibromide (970 mg, 4.31 mmol) and ethanol (0.25 mL, 4.31 mmol), and the mixture was stirred for 18 h. The reaction mixture was quenched by addition of water (20.0 mL) and the resulting mixture was stirred for 2 h. To this mixture was added 1.00 M NaOH (30.0 mL) and extracted with DCM (3×100 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by flash chromatography (10 to 30% Methanol/DCM) to afford the title compound (438 mg, 95%) as a colorless oil. LC/MS: Rt=0.89 min, ES+ 205.2 (AA standard).

Workup

  1. customThe reaction mixture was quenched by addition of water (20.0 mL)
  2. stirringthe resulting mixture was stirred for 2 h
  3. additionTo this mixture was added 1.00 M NaOH (30.0 mL)
  4. extractionextracted with DCM (3×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue was purified by flash chromatography (10 to 30% Methanol/DCM)

Sources & evidence

ORD record
ord-9ba8ddd2c26542e3a32ed8519099b2d7
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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