Ethanol → ethyl 6-benzyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate
Reaction equation
[N:1]1(C(OC(C)(C)C)=O)[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.[BH4-].[Na+]>CN(C=O)C>[CH2:22]([N:7]1[CH2:8][CH2:9][C:4]2[CH:3]=[C:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:1][C:5]=2[CH2:6]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-tert-butyl 2-ethyl 1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate (1.0 eq) in DMF was added benzyl bromide (1.0 eq.) and heated to 80° C. for 4 hrs. Reaction mixture was evaporated to dryness. The product obtained was dissolved aqueous ethanol and NaBH4 (1.5 eq.) was added at 0° C. and stirred for 4 hrs. Reaction was quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded ethyl 6-benzyl-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate.
Workup
- customReaction mixture
- customwas evaporated to dryness
- customThe product obtained
- additionwas added at 0° C.
- customReaction
- customwas quenched with water
- extractionextracted with dichloromethane
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
- customto afford crude product, which
- customon purification by column chromatography
Sources & evidence
- ORD record
- ord-212ac8f8efbd4c6b86dfe6d5c1f68252
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440830B2
Reaction notes
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