Ethylenediamine → HCID 10431217, compound

HRID 2414284Notes

Reaction equation

HRID 2414284 reaction equation
[BH4-].[Na+].C(N)CN.[CH3:7][O:8][C:9](=[O:35])[CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][N:16]1[C@@H:20]([CH2:21][O:22][C:23](=[O:33])[NH:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH2:18][C:17]1=[O:34]>C(O)C.[Ni](Cl)Cl>[CH3:7][O:8][C:9](=[O:35])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][N:16]1[C@@H:20]([CH2:21][O:22][C:23](=[O:33])[NH:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][CH2:18][C:17]1=[O:34]

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 10023919HCID 10023919, compound

Product 1

HCID 10431217HCID 10431217, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent2×

Procedure

95% Ethanol (1.0 mL) was added to a slowly stirred mixture of nickel (II) chloride (86 mg, 0.66 mmol) and sodium borohydride (12 mg, 0.33 mmol) under nitrogen. The mixture immediately turned black. After 15 min, ethylenediamine (70 μL, 1.04 mmol) was added. After an additional 15 min, a solution of alkyne 13 (53 mg, 0.13 mmol) in 95% ethanol (1.0 mL) was added. The flask was evacuated and refilled with hydrogen (3×), and the reaction mixture was stirred vigorously under a balloon of hydrogen for 22 h. The mixture was then filtered through celite, washing with MeOH (5 mL) and the filtrate was concentrated in vacuo. Purification of the residue by flash column chromatography on silica (100% CH2Cl2→50% EtOAc/CH2Cl2, gradient) afforded 30 mg (56%) of the title compound (15).

Workup

  1. waitAfter an additional 15 min
  2. customThe flask was evacuated
  3. additionrefilled with hydrogen (3×)
  4. filtrationThe mixture was then filtered through celite
  5. washwashing with MeOH (5 mL)
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica (100% CH2Cl2→50% EtOAc/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-d1f6438029e045ccbd9245a2108e126d
Source dataset
uspto-grants-2004_11
Patent number
US06812240B1

Reaction notes

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