2-Methoxyethylamine → HCID 67311514, compound

HRID 1787867Notes

Reaction equation

HRID 1787867 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=O.C(N=C=NC(C)C)(C)C.[CH3:23][O:24][CH2:25][CH2:26][NH2:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:42](=O)/[CH:43]=[CH:44]/[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(O)(=O)C>[CH3:23][O:24][CH2:25][CH2:26][N:27]([CH2:1][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)[CH2:42][CH:43]=[CH:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

9

Reactant 5

HCID 80182-MethoxyethylamineHCID 12734DiisopropylcarbodiimideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 637511CinnamaldehydeHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 67311514HCID 67311514, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Wang resin (1.1 mmol/g, 1.00 g) in a polypropylene filtration tube with a polyethylene frit was added DMF (5 mL) and CH2Cl2 (5 mL), followed by 4-formylcinnamic acid (5.5 mmol, 969 mg), DMAP (1.08 mmol, 132 mg) and diisopropylcarbodiimide (5.5 mmol, 861 μL). The mixture was shaken at room temperature for 24 hours. The resulting resin was washed with DMF (3×mL), MeOH (3×5 mL) and CH2Cl2 (4×5 mL), then dried in vacuo. To the resin (100 mg) was added 2-methoxyethylamine (1.1 mmol, 96 μL) in DMF (1 mL), Na(OAc)3BH (2.2 mmol, 466 mg) and acetic acid (25 μL). After shaking at room temperature overnight, the resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL), then dried in vacuo. The resulting resin was suspended in a solution of trans-cinnamaldehyde (1.1 mmol, 139 μL), Na(OAc)3BH (2.2 mmol, 466 mg) and acetic acid (10 μL) in DMF (1 mL). The mixture was shaken at room temperature for 24 hours. The resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL), then dried in vacuo. To the dry resin was added polyamine resin and CH2Cl2. The mixture was agitated at room temperature for 24 hours, then filtered and washed with CH2Cl2 (2×1.5 mL). The filtrates were collected and evaporated to yield 21 as a colorless oil (LRMS m/z 351).

Workup

  1. filtrationWang resin (1.1 mmol/g, 1.00 g) in a polypropylene filtration tube with a polyethylene frit
  2. additionwas added DMF (5 mL) and CH2Cl2 (5 mL)
  3. washThe resulting resin was washed with DMF (3×mL), MeOH (3×5 mL) and CH2Cl2 (4×5 mL)
  4. customdried in vacuo
  5. stirringAfter shaking at room temperature overnight
  6. washthe resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL)
  7. customdried in vacuo
  8. stirringThe mixture was shaken at room temperature for 24 hours
  9. washThe resulting resin was washed with DMF (3×1 mL), MeOH (3×1 mL) and CH2Cl2 (4×1 mL)
  10. customdried in vacuo
  11. additionTo the dry resin was added polyamine resin and CH2Cl2
  12. stirringThe mixture was agitated at room temperature for 24 hours
  13. filtrationfiltered
  14. washwashed with CH2Cl2 (2×1.5 mL)
  15. customThe filtrates were collected
  16. customevaporated

Sources & evidence

ORD record
ord-c1db8e4ae1b249e1809a6b8b9ce4932b
Source dataset
uspto-grants-2009_03
Patent number
US07511073B2

Reaction notes

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