Methanesulfonic Acid → HCID 131713900, compound

HRID 1632581Notes

Reaction equation

HRID 1632581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)[CH:6]=[CH:5][C:4]=1[OH:34].[CH2:35]([O:42][CH:43]1[N:47]2[C:48]3[C:53]([C:54]([CH2:57][C:58]#[N:59])(O)[CH2:55][CH:46]2[CH2:45][CH2:44]1)=[CH:52][CH:51]=[C:50]([CH:60]([CH3:68])[CH:61](C)CCCCC)[CH:49]=3)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.CS(O)(=O)=O.[OH-].[Na+]>O1CCCC1>[CH3:33][O:32][C:27]1[CH:26]=[C:25]([CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9][C:7]2[CH:6]=[CH:5][C:4]([OH:34])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:30]=[CH:29][C:28]=1[OH:31].[CH2:35]([O:42][CH:43]1[N:47]2[C:48]3[C:53]([C:54](=[CH:57][C:58]#[N:59])[CH2:55][CH:46]2[CH2:45][CH2:44]1)=[CH:52][CH:51]=[C:50]([C:60]([CH3:61])([CH3:68])[CH2:7][CH2:8][CH2:3][CH2:4][CH2:5][CH3:6])[CH:49]=3)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 131713902HCID 131713902, compound

Product 1

HCID 131713900HCID 131713900, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.9 g. (23.7 mmole) dl-6-benzyloxy-5-cyanomethyl-5-hydroxy-8-(1,2-dimethylheptyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]quinoline in 250 ml. dry tetrahydrofuran is added a few grams of molecular sieves and 2.30 g. (23.9 mmole) methanesulfonic acid. The mixture is stirred for 16 hours at room temperature, made alkaline with sodium hydroxide solution, washed with water, the organic layer dried (MgSO4) and the solvent evaporated in vacuo to afford the crude product which was used in the next step.

Workup

  1. washwashed with water
  2. dry with materialthe organic layer dried (MgSO4)
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5ad449dcda764612a56634d16c79efe2
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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