N-BOC-ethylenediamine → HCID 86722958, compound

HRID 1404354Notes

Reaction equation

HRID 1404354 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[CH2:10][C:11]1([OH:18])[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([NH:27][CH2:28][CH2:29][NH2:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH2:1]([O:8][C:9](=[O:19])[CH2:10][C:11]1([OH:18])[CH2:16][CH2:15][CH:14]([NH:30][CH2:29][CH2:28][NH:27][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 86722957HCID 86722957, compound

Product 1

HCID 86722958HCID 86722958, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium ethoxide (0.47 mL, 2.24 mmol) was added to a solution of (1-Hydroxy-4-oxo-cyclohexyl)-acetic acid benzyl ester (1.22 g, 4.65 mmol) and 2-(Boc-amino)ethylamine (0.97 g, 6.05 mmol) in DCM (5.0 mL) under argon. The reaction was stirred at RT for 5 hr. The reaction was concentrated in vacuo. The residue was diluted with methanol (23 mL) under argon and cooled to −78° C. Sodium triacetoxyborohydride (1.49 g, 7.03 mmol) was added in one portion and the reaction allowed to slowly warm to RT overnight. The reaction was quenched with 10% Na2CO3 and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 407 (MH)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionThe residue was diluted with methanol (23 mL) under argon
  3. temperaturecooled to −78° C
  4. temperatureto slowly warm to RT overnight
  5. customThe reaction was quenched with 10% Na2CO3
  6. extractionextracted with ethyl acetate (2×)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-0c9c56f6e89547d398cda76e4e88b9b4
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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