Sodium Hydroxide → 4-(2-Benzyloxy-ethyl)-2,2,6,6-tetramethyl-morpholine

HRID 601558Notes

Reaction equation

HRID 601558 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6]([CH3:9])([CH3:8])[CH2:5][NH:4][CH2:3]1.[CH2:11]([O:18][CH2:19][CH:20]=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH2:11]([O:18][CH2:19][CH2:20][N:4]1[CH2:5][C:6]([CH3:9])([CH3:8])[O:7][C:2]([CH3:10])([CH3:1])[CH2:3]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 108989(Phenylmethoxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 198280762,2,6,6-Tetramethylmorpholine

Product 1

HCID 574214984-(2-Benzyloxy-ethyl)-2,2,6,6-tetramethyl-morpholineYield 63.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve 500 mg (2.79 mmol) of 2,2,6,6-tetramethyl-morpholine (500 mg, 2.79 mmol) in dichloroethane (10 mL). Add benzyloxy-acetaldehyde (470 μl, 3.35 mmol) and stir at room temperature for 20 min. Add sodium triacetoxyborohydride (770 mg, 3.63 mmol) and continue stirring at room temperature for 20 h. Pour the reaction mixture into 100 mL of 1N NaOH (100 mL) and extract with CH2Cl2 (2×100 mL). Wash the combined organic layers with brine (100 mL). Purify using silica gel chromatography, using a gradient of 0% to 10% (2N NH3 in MeOH)/CHCl3 as eluent, to give 490 mg (63%) of the desired product. MS (ES+) 278.3 (M+1)+.

Workup

  1. extractionextract with CH2Cl2 (2×100 mL)
  2. washWash the combined organic layers with brine (100 mL)
  3. customPurify

Sources & evidence

ORD record
ord-4fac93e20abb4020b44fb0bc944f9fee
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

Loading…