Acetic Acid → HCID 43512818, compound

HRID 2167105Notes

Reaction equation

HRID 2167105 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[O:11]1[C:16]2[CH:17]=[CH:18][C:19]([NH2:21])=[CH:20][C:15]=2[O:14][CH2:13][CH2:12]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl.C(OCC)(=O)C>[O:11]1[C:16]2[CH:17]=[CH:18][C:19]([NH:21][CH:2]3[CH2:3][C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[CH2:1]3)=[CH:20][C:15]=2[O:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 119832-IndanoneHCID 891481,4-Benzodioxan-6-ylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43512818HCID 43512818, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-indanone (2 g, 15.1 mmol) in DCE (50 mL) were added 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (2.28 g, 15.1 mmol), Na(OAc)3BH (4.81 g, 22.6 mmol), AcOH (1.8 mL) successively at 0° C. and the mixture was stirred overnight at rt. The reaction mixture was dissolved in ethyl acetate and was washed with 1N NaOH, water and brine. The solution was dried over Na2SO4, filtered and concentrated. The crude material was purified by Combiflash® chromatography eluting with 9-10% ethyl acetate-hexane to get compound 57.

Workup

  1. washwas washed with 1N NaOH, water and brine
  2. dry with materialThe solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by Combiflash® chromatography
  6. washeluting with 9-10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c0978133bd784115b2beab6c61b5d798
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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