Methanol → HCID 178461167, compound

HRID 1374438Notes

Reaction equation

HRID 1374438 reaction equation
[CH3:1][C@H:2]1[CH:6]=[C:5]([C:7]2[N:8]=[C:9]([SH:12])[S:10][CH:11]=2)[CH2:4][N:3]1[C:13](OCC=C)=O.ClCC(C1CN(C(OCC=C)=O)[C@@H](C)C=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO>C1COCC1>[CH3:13][N:3]1[C@@H:2]([CH3:1])[CH:6]=[C:5]([C:7]2[N:8]=[C:9]([SH:12])[S:10][CH:11]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11021108HCID 11021108, compoundHCID 21226445Aluminium lithium hydrideHCID 178459645HCID 178459645, compound

Product 1

HCID 178461167HCID 178461167, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Allyl (2S)-2-methyl-4-(2-sulfanyl-1,3-thiazol-4-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate prepared from allyl (2S)-4-(chloroacetyl)-2-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate (331 mg, 1.36 mmol) in the same manner as Reference example 2.e) was dissolved in THF (3 ml). The solution was dropped into a suspension of LiAlH4 (103 mg, 2.71 mmol) in THF (3 ml) at 0° C. and the mixture was stirred at room temperature for 10 minutes. Thereto was added methanol and the mixture was filtered through a pad of silica gel. The solvent was removed in vacuo and the residue was purified with silica gel chromatography to give 4-[((5S)-1,5-dimethyl-2,5-dihydro-1H-pyrrol-3-yl]-1,3-thiazole-2-thiol (224 mg, 77%).

Workup

  1. filtrationthe mixture was filtered through a pad of silica gel
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-0ed5cf6b64944f58a4cf46c17cf8a8a1
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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