Water → HCID 67201523, compound

HRID 547958Notes

Reaction equation

HRID 547958 reaction equation
[CH2:1]([Si:3](Cl)([CH2:6]C)[CH2:4]C)C.[OH:9][CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][CH:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH2:18]3)[N:13]([CH3:14])[CH2:12]1.C(N(CC)CC)C.O>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH3:6][Si:3]([CH3:1])([CH3:4])[O:9][CH2:10][C@@H:11]1[CH:26]=[C:25]2[C@@H:15]([CH2:16][C:17]3[C:27]4[C:20](=[CH:21][CH:22]=[CH:23][C:24]2=4)[NH:19][CH:18]=3)[N:13]([CH3:14])[CH2:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 22803977HCID 22803977, compound

Product 1

HCID 67201523HCID 67201523, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Triethylsilyl chloride (TES-Cl, 1.30 g) is added into a mixture of dihydrolysergol (1.47 g), triethylamine (1.74 g) and DMAP (0.14 g) in N,N-dimethylformamide (10 mL) and the mixture is stirred at room temperature. After complete reaction, the mixture is cooled and water (15 mL) is added. The resulted suspension is stirred for an additional 2 h and then filtered and washed with water. The product is dried and recrystallized from dichloromethane/heptanes to give 1.47 g of 8β-(trimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline in 70% yield.

Workup

  1. customAfter complete reaction
  2. temperaturethe mixture is cooled
  3. stirringThe resulted suspension is stirred for an additional 2 h
  4. filtrationfiltered
  5. washwashed with water
  6. customThe product is dried
  7. customrecrystallized from dichloromethane/heptanes

Sources & evidence

ORD record
ord-d2d05cb3f3a649a9ae84ac0a8a347300
Source dataset
uspto-grants-2011_05
Patent number
US07939665B2

Reaction notes

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