Acetic Acid → 4-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]morpholine

HRID 1820295Notes

Reaction equation

HRID 1820295 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:15]([CH2:33][CH2:34][C:35]1([C:41](=O)[CH3:42])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.C(O)(=O)C.C(=O)([O-])O.[Na+]>ClCCCl.C(Cl)(Cl)Cl>[O:15]([CH2:33][CH2:34][C:35]1([CH2:41][CH2:42][N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[Si:16]([C:29]([CH3:31])([CH3:30])[CH3:32])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 231098901-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]acetaldehyde

Product 1

HCID 574278614-[2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]morpholineYield 138.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

After adding sodium triacetoxyborohydride (0.63 g, 2.98 mmol) to a solution of 1-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]acetaldehyde (1.29 g, ca. 1.97 mmol), morpholine (0.26 mL, 2.98 mmol) and acetic acid (0.23 mL, 4.02 mmol) in 1,2-dichloroethane (5 mL), the mixture was stirred at room temperature for 2.5 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with chloroform. The organic layer was washed with saturated brine and dried (anhydrous sodium sulfate), and then the solvent was distilled off under reduced pressure to obtain the title compound as a brown oil (1.31 g). This was used without purification for the following step.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried (anhydrous sodium sulfate)
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cc7dbf41685c4c70aec1e9bf7d085201
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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