Water → HCID 59841556, compound

HRID 547956Notes

Reaction equation

HRID 547956 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH: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.C(N(CC)CC)C.O>CN(C)C=O>[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)[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 149871413-67-8HCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 59841556HCID 59841556, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyldimethylsilyl chloride (TBS-Cl, 19.6 g) is added into a mixture of Lysergol (30 g) and triethylamine (16.7 g) in N,N-dimethylformamide (150 mL) and the mixture is stirred at room temperature for 2-3 h. The mixture is cooled and water (240 mL) is added. The resulting suspension is stirred for an additional 2 h and then filtered and washed with water. The product is dried under vacuum to give 42 g of 8β-(tert-butyldimethylsiloxymethyl)-9,10-didehydro-6-methyl-ergoline in 96.5% yield.

Workup

  1. temperatureThe mixture is cooled
  2. stirringThe resulting suspension is stirred for an additional 2 h
  3. filtrationfiltered
  4. washwashed with water
  5. customThe product is dried under vacuum

Sources & evidence

ORD record
ord-52a40d20c789440bb37639adfcd824c3
Source dataset
uspto-grants-2011_05
Patent number
US07939665B2

Reaction notes

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