4-Methoxybenzylamine → HCID 66798735, compound

HRID 1193309Notes

Reaction equation

HRID 1193309 reaction equation
[CH3:1][C:2]1([CH3:13])[C:11](=O)[CH2:10][CH2:9][C:4]2([O:8][CH2:7][CH2:6][O:5]2)[CH2:3]1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][CH:11]2[CH2:10][CH2:9][C:4]3([O:8][CH2:7][CH2:6][O:5]3)[CH2:3][C:2]2([CH3:13])[CH3:1])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 111713897,7-diMethyl-1,4-dioxaspiro[4.5]decan-8-one

Product 1

HCID 66798735HCID 66798735, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7,7-Dimethyl-1,4-dioxaspiro[4.5]decan-8-one (2.8 g, 15.217 mmol, 1 eq) and 4-methoxy-benzylamine (2.08 g, 15.217 mmol, 1 eq) were dissolved in dichloromethane (100 ml) and stirred for 3 h at RT. Na(OAc)3BH (9.67 g, 45.65 mmol, 3 eq) was added in portions at 0° C., and stirring was carried out for 20 h at RT. The reaction solution was diluted with dichloromethane (100 ml), washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (Alox neutral, 10% ethyl acetate in hexane). Yield: 46% (2.13 g, 6.98 mmol).

Workup

  1. stirringstirring
  2. waitwas carried out for 20 h at RT
  3. washwashed with water (100 ml) and sat. NaCl solution (100 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (Alox neutral, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-18282379413e43e2af15fa1787db6817
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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