Triethylamine → HCID 70406371, compound

HRID 414206Notes

Reaction equation

HRID 414206 reaction equation
[NH2:1][C@H:2]1[CH:16]=[C:15]2[C@@H:5]([CH2:6][C:7]3[C:17]4[C:10](=[CH:11][CH:12]=[CH:13][C:14]2=4)[NH:9][CH:8]=3)[N:4]([CH3:18])[CH2:3]1.C(N(CC)CC)C.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[CH3:18][N:4]1[C@H:5]2[C:15]([C:14]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:17]=3[C:7]([CH2:6]2)=[CH:8][NH:9]4)=[CH:16][C@H:2]([NH:1][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 106576389,10-Didehydro-6-methylergolin-8alpha-amine

Product 1

HCID 70406371HCID 70406371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 5.5 g 8α-amino-6-methyl-9,10-didehydro-ergoline in 200 ml CH2Cl2 is cooled to 0° and treated with 6.44 ml triethylamine followed by dropwise addition of 2.97 ml pivaloyl chloride. The mixture is stirred for 2 hours at room temperature and washed with water. The organic layer is dried (Na2SO4) and evaporated. The residue is chromatographed on 200 g silica gel using 98:2 CH2Cl2 /CH3OH and then crystallized from ether to yield 6-methyl-8α-pivaloylamino-9,10-didehydro-ergoline, m.p. 158°-159°.

Workup

  1. temperatureis cooled to 0°
  2. washwashed with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customevaporated
  5. customThe residue is chromatographed on 200 g silica gel using 98:2 CH2Cl2 /CH3OH
  6. customcrystallized from ether

Sources & evidence

ORD record
ord-0a5afd457cc642a581ed07cdd00190af
Source dataset
uspto-grants-1988_12
Patent number
US04791115

Reaction notes

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