Sodium Carbonate → 8-(3-Methoxybenzyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 2167507Notes

Reaction equation

HRID 2167507 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[O:11]1[C:15]2([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:18]1[CH2:19][CH2:20][C:15]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 115693-MethoxybenzaldehydeHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 64703878-(3-Methoxybenzyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-methoxybenzaldehyde (10.0 g, 73.4 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (10.5 g, 73.4 mmol), sodium triacetoxyborohydride (20.2 g, 95.3 mmol), and acetic acid (4.2 mL), in methylene chloride (400 mL), was stirred at ambient temperature. After 19 h, a 2 N aqueous sodium carbonate solution (220 mL) was added portionwise. After stirring for 15 min, the aqueous layer was separated and extracted with methylene chloride (100 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuo to provide 8-(3-methoxybenzyl)-1,4-dioxa-8-azaspiro[4.5]decane (18.3 g, 95%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) δ 7.25-7.19 (m, 1H), 6.91-6.89 (m, 2H), 6.80-6.77 (m, 1H), 3.94 (s, 4H), 3.80 (s, 3H), 3.50 (s, 2H), 2.53-2.49 (m, 4H), 1.76-1.72 (m, 4H).

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with methylene chloride (100 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7788a472b76a445d977d36ce639e3145
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

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