Iodine → Benzyl 3-formylpiperidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:4]1.C([O-])(O)=O.[Na+].II.CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl.O.CO>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:4]1)=[O:1]Participants
Procedure
A 500-mL round-bottomed flask was charged a solution of benzyl 3-(hydroxymethyl)piperidine-1-carboxylate (8.94 g, 35.90 mmol, 1.00 equiv) in DCM (200 mL), NaHCO3 (9.05 g, 107.74 mmol, 3.00 equiv) in H2O (80 mL), I2 (18.24 g, 71.81 mmol, 2.00 equiv) and TEMPO (570 mg, 3.65 mmol, 0.10 equiv). The resulting mixture was stirred for 18 hours at room temperature. The reaction progress was monitored by TLC (DCM:MeOH=20:1). Upon completion, the reaction was then quenched by the addition of 10 mL of NaHSO3/H2O. The pH was adjusted to 8 with NaHCO3. The resulting solution was extracted with dichloromethane (3×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator to afford benzyl 3-formylpiperidine-1-carboxylate as brown oil (6.2 g, (70%).
Workup
- customUpon completion, the reaction was then quenched by the addition of 10 mL of NaHSO3/H2O
- extractionThe resulting solution was extracted with dichloromethane (3×50 mL)
- dry with materialCombined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered off
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-f1f45213721e49ed8aed2baaad3769b3
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080566B1
Reaction notes
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