5-tert-Butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate → 1,1-Dimethylethyl 6,7-dihydro-2-(hydroxymethyl)thieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388686Notes

Reaction equation

HRID 2388686 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[C:15]2[CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=2[CH:9]=[C:8]1[C:23](OCC)=[O:24].C(OCC)(=O)C.CCCCCC>O1CCCC1>[OH:24][CH2:23][C:8]1[S:7][C:15]2[CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 118454155-tert-Butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylateHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 118456061,1-Dimethylethyl 6,7-dihydro-2-(hydroxymethyl)thieno[3,2-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrahydrofuran (10 ml) was added dropwise to lithium aluminium hydride (0.46 g, 2 eq.) at 0° C. and the mixture was stirred for 10-15 min at the same temperature. Then a solution of 5-tert-butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate (2 g, 0.006 mol) in tetrahydrofuran (10 ml) was added dropwise to the mixture at 0° C. and the resulting reaction mixture was stirred for 1-2 h at the same temperature. Progress of the reaction was monitored by TLC (30% ethyl acetate/hexane). Upon completion of the reaction the reaction mixture was poured into ice water and quenched with saturated sodium sulfate solution at 0° C. The mixture was filtered over a bed of Celite and the filtrate was extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield the crude product as a pale yellow colored liquid. The crude product obtained was directly employed in the next step. Yield: 1.6 g (92%).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred for 1-2 h at the same temperature
  3. customUpon completion of the reaction the reaction mixture
  4. customquenched with saturated sodium sulfate solution at 0° C
  5. filtrationThe mixture was filtered over a bed of Celite
  6. extractionthe filtrate was extracted with ethyl acetate (2×150 ml)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto yield the crude product as a pale yellow colored liquid

Sources & evidence

ORD record
ord-d09b47db42f14825982153229b4eeaa6
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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