Methanol → 1,1-Dimethylethyl 6,7-dihydro-2-(hydroxymethyl)thieno[3,2-c]pyridine-5(4H)-carboxylate
Reaction equation
CC(C[AlH]CC(C)C)C.[S:10]1[C:18]2[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C:13]=2[CH:12]=[C:11]1[C:26](OC)=[O:27].CO.[Cl-].[Na+]>C1(C)C=CC=CC=1>[OH:27][CH2:26][C:11]1[S:10][C:18]2[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C:13]=2[CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
DIBAL-H (11.1 mmol) was added to a −78° C. cold solution of 5-tert-butyl 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate (1.5 g, 5.3 mmol) in dry toluene (30 ml). The reaction mixture obtained was stirred at −78° C. for 1.5 hours. The course of the reaction was monitored by thin layer chromatography. Methanol (12 ml) was then added to the reaction mixture, the mixture was warmed slowly to 25° C. and thereafter saturated sodium chloride solution was added. The reaction mixture was filtered over Celite and the filter cake was washed with ethyl acetate. The organic phases were concentrated under reduced pressure. The crude product obtained in this way was employed in the next stage without further purification. The crude yield was 1.4 g.
Workup
- customThe reaction mixture obtained
- temperaturethe mixture was warmed slowly to 25° C.
- filtrationThe reaction mixture was filtered over Celite
- washthe filter cake was washed with ethyl acetate
- concentrationThe organic phases were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5cc545b301af4ae4b62d9c61153f3f12
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268814B2
Reaction notes
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