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

HRID 2167513Notes

Reaction equation

HRID 2167513 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)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[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 5

HCID 176Acetic AcidHCID 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 82.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-methoxybenzaldehyde (10.0 g, 73.4 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (21.0 g, 146.9 mmol), sodium triacetoxyborohydride (31.1 g, 146.9 mmol), and acetic acid (4.4 mL, 73.45 mmol) in 1,2-dichloroethane (100 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 (200 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to provide 8-(3-methoxybenzyl)-1,4-dioxa-8-azaspiro[4.5]decane (16.0 g, 82%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 7.27-7.20 (m, 1H), 6.93-6.88 (m, 2H), 6.79 (dd, J=2.4, 8.2 Hz, 1H), 3.94 (s, 4H), 3.82-3.78 (m, 3H), 3.50 (s, 2H), 2.56-2.47 (m, 4H), 1.74 (t, J=5.6 Hz, 4H); ESI MS (m/z) 264 [M+H].

Workup

  1. stirringAfter stirring for 15 min
  2. customthe aqueous layer was separated
  3. extractionextracted with methylene chloride (200 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67e75fa270eb48eabeb5070e4db10e69
Source dataset
uspto-grants-2015_06
Patent number
US09045468B2

Reaction notes

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