Trimethylamine → HCID 86702741, compound

HRID 511751Notes

Reaction equation

HRID 511751 reaction equation
CN(C)C.[CH2:5]([C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH2:14][CH3:15])[C:8]=1[C:16]1[C:17](=[O:30])[CH:18]2[CH:22]([C:23]=1[OH:24])[CH2:21][CH:20]([CH:25]([O:28][CH3:29])[O:26][CH3:27])[CH2:19]2)[CH3:6].Cl[C:32]([O:34][CH2:35][CH3:36])=[O:33]>ClCCl>[C:32](=[O:33])([O:34][CH2:35][CH3:36])[O:30][C:17]1[CH:18]2[CH:22]([CH2:21][CH:20]([CH:25]([O:26][CH3:27])[O:28][CH3:29])[CH2:19]2)[C:23](=[O:24])[C:16]=1[C:8]1[C:9]([CH2:14][CH3:15])=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 10928Ethyl chloroformateHCID 67511136HCID 67511136, compound

Product 1

HCID 86702741HCID 86702741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At room temperature, 80 mg (0.80 mmol) of trimethylamine are added dropwise to 0.090 g (0.25 mmol) of 2-(2,6-diethyl-4-methylphenyl)-5-(dimethoxymethyl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-one (compound I-a-9 according to the invention) and 30 mg (0.28 mmol) of ethyl chloroformate in 15 ml of dichloromethane, and the mixture is stirred for another 1 h. The mixture is poured onto ice-water, taken up in dichloromethane, washed with water, dried (magnesium sulphate), and the solvent is distilled off.

Workup

  1. additionThe mixture is poured onto ice-water
  2. washwashed with water
  3. dry with materialdried (magnesium sulphate)
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-26c791c721694f8eaa84e8059093c695
Source dataset
uspto-grants-2015_08
Patent number
US09101133B2

Reaction notes

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