Sodium Hydroxide → N-(cyclohexylmethyl)-2,2-diethoxyethanamine

HRID 43254

Reaction equation

HRID 43254 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][NH2:6])[CH3:2].[CH:10]1([CH:16]=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CC1OCCC1>[CH:10]1([CH2:16][NH:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 695242,2-DiethoxyethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 60052150N-(cyclohexylmethyl)-2,2-diethoxyethanamine

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

To a mixture of 2,2-diethoxyethylamine (209 mL, 1.43 mol) and MeTHF (1050 L) was added cyclohexanecarbaldehyde (107 mL, 0.89 mol). The reaction mixture was stirred for 30 min at room temperature and cooled to 0° C. Sodium triacetoxyborohydride (378 g, 1.79 mol) was added over 40 min and the reaction mixture was stirred for 2 h and cooled to 0° C. 1 M NaOH (1 L) was added. The organic layer was washed with brine in water (1:1, 2×1 L) and the volume was reduced to ˜20%. MeTHF (1 L) was added and the volume reduced to ˜20%. The solution of the crude title intermediate was used directly in the next step.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred for 2 h
  3. temperaturecooled to 0° C
  4. washThe organic layer was washed with brine in water (1:1, 2×1 L)
  5. additionMeTHF (1 L) was added

Sources & evidence

ORD record
ord-2ae19a871ca64856a3312bef045f65b0
Source dataset
uspto-grants-2013_09
Patent number
US08536335B2

Linked notes

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