Acetone → Methyl 2,3-dihydro-2-(1-methylethyl)-1H-isoindole-1-acetate

HRID 1371524Notes

Reaction equation

HRID 1371524 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][NH:6]1.[CH3:15][C:16]([CH3:18])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.[OH-].[Na+]>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[CH:16]([CH3:18])[CH3:15]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 58777828Methyl (2,3-dihydro-1H-isoindol-1-yl)acetate

Product 1

HCID 69219063Methyl 2,3-dihydro-2-(1-methylethyl)-1H-isoindole-1-acetate

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To the compound obtained from Step A (0.50 g, 2.61 mmol) in dichloroethane (46 mL) was added acetone (1.76 mL, 24.01 mmol) and sodium triacetoxyborohydride (2.48 g., 11.74 mmol). After 6 hours, the mixture was diluted with 1.0N NaOH (100 mL), and the organic portion was separated. The aqueous layer was extracted with DCM (3×100 mL). The combined DCM extracts were dried (MgSO4) and concentrated to dryness to afford about 0.60 g (99%). EIS-MS 235 [M+1].

Workup

  1. customthe organic portion was separated
  2. extractionThe aqueous layer was extracted with DCM (3×100 mL)
  3. dry with materialThe combined DCM extracts were dried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customto afford about 0.60 g (99%)

Sources & evidence

ORD record
ord-0517601f3f594889a0b22ea472a9ce9b
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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