Diethyl (2-aminoethyl)phosphonate oxalate → HCID 178476908, compound

HRID 2404106Notes

Reaction equation

HRID 2404106 reaction equation
C(O)(=O)C(O)=O.[CH2:7]([O:9][P:10]([CH2:15][CH2:16][NH2:17])(=[O:14])[O:11][CH2:12][CH3:13])[CH3:8].[C:18]([CH:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[CH:35]=[C:34]([CH:39]=O)[CH:33]=[CH:32]3)[CH2:24][CH2:23]1)([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:12]([O:11][P:10]([CH2:15][CH2:16][NH:17][CH2:39][C:34]1[CH:33]=[CH:32][C:31]2[C:36](=[CH:37][CH:38]=[C:29]([O:28][C@H:25]3[CH2:26][CH2:27][C@H:22]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:23][CH2:24]3)[CH:30]=2)[CH:35]=1)(=[O:14])[O:9][CH2:7][CH3:8])[CH3:13]

Participants

5

Reactant 3

HCID 2733595Diethyl (2-aminoethyl)phosphonate oxalateHCID 5049666Sodium triacetoxyborohydrideHCID 866684126-(trans-4-Tert-butylcyclohexyloxy)-2-naphthaldehyde

Product 1

HCID 178476908HCID 178476908, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2-amino-ethyl)-phosphonic acid diethyl ester oxalic acid salt (200 mg, 0.74 mmol) in 1,2-dichloroethane (3 mL) was added 6-(4-tert-butyl-cyclohexyloxy)-naphthalene-2-carbaldehyde (343 mg, 1.1 mmol). The mixture was stirred at room temperature for 1 hour, then sodium triacetoxyborohydride (329 mg, 1.5 mmol) was added. After being stirred at room temperature overnight, the reaction mixture was quenched with water, stirred at room temperature for 30 min, then diluted with ethyl acetate, and washed with aqueous NaHCO3. The organic layer was dried over MgSO4 and purified with a silica gel column eluted with ethyl acetate (100%), then eluted with methanol in dichloromethane from 0 to 15% to give sticky oil (130 mg, yield: 25%). ESI-MS: 476.3 (M+H)+.

Workup

  1. stirringAfter being stirred at room temperature overnight
  2. customthe reaction mixture was quenched with water
  3. stirringstirred at room temperature for 30 min
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous NaHCO3
  6. dry with materialThe organic layer was dried over MgSO4
  7. custompurified with a silica gel column
  8. washeluted with ethyl acetate (100%)
  9. washeluted with methanol in dichloromethane from 0 to 15%

Sources & evidence

ORD record
ord-dc910e067f7f428aa16ce51c097332f0
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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