Acetic Acid → 2-(2,6-dichlorophenyl)-N-(spiro[2.5]octan-6-ylmethyl)-2-((triethylsilyl)oxy)ethanamine

HRID 2202685Notes

Reaction equation

HRID 2202685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH2:10][NH2:11].[CH2:20]1[C:22]2([CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]2)[CH2:21]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]([O:12][Si:13]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:18][CH3:19])[CH2:10][NH:11][CH2:28][CH:25]1[CH2:26][CH2:27][C:22]2([CH2:20][CH2:21]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 86598198Spiro(2.5)octane-6-carbaldehydeHCID 1238562512-(2,6-Dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine

Product 1

HCID 1233531822-(2,6-dichlorophenyl)-N-(spiro[2.5]octan-6-ylmethyl)-2-((triethylsilyl)oxy)ethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,6-dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine (248 mg, 0.774 mmol) in DCM (2581 μl) was added spiro[2.5]octane-6-carbaldehyde (107 mg, 0.774 mmol), AcOH (35.5 μl, 0.619 mmol) and NaBH(OAc)3 (246 mg, 1.161 mmol). The slurry mixture was stirred at room temperature for overnight. The mixture was quenched with 0.5 M NaOH and mixture was stirred at rt for 30 min. Evolution of gas was observed. The layers were separated. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluting with a gradient of 0% to 100% EtOAc in hexane to give 2-(2,6-dichlorophenyl)-N-(spiro[2.5]octan-6-ylmethyl)-2-((triethylsilyl)oxy)ethanamine

Workup

  1. customThe mixture was quenched with 0.5 M NaOH and mixture
  2. stirringwas stirred at rt for 30 min
  3. customThe layers were separated
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a gradient of 0% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-57d7248a90594ea79af9d509b20c6609
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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