Sodium Bicarbonate → 3,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

HRID 1480370Notes

Reaction equation

HRID 1480370 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:28])[O:18][CH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:17]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)=[O:28])[CH:11]([CH3:15])[CH2:10]1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 83918261tert-Butyl N-[(2-methylpiperidin-4-yl)methyl]carbamate

Product 1

HCID 867226283,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising tert-butyl((2-methylpiperidin-4-yl)methyl)carbamate (step 2) (1.15 g, 5.04 mmol) and 3,5-dichlorobenzyl carbonochloridate (1.327 g, 5.54 mmol) in DCM (15 ml) was treated with aq. saturated sodium bicarbonate (0.504 ml, 5.04 mmol) and stirred at room temperature for 18 hours. The organic portion was separated and the aqueous phase extracted with DCM (2×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Further purification by chromatography on silica, eluting in 0-20% 2M ammonia in MeOH in DCM afforded the title compound;

Workup

  1. customThe organic portion was separated
  2. extractionthe aqueous phase extracted with DCM (2×10 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customFurther purification by chromatography on silica
  7. washeluting in 0-20% 2M ammonia in MeOH in DCM

Sources & evidence

ORD record
ord-667d50e1f7f34a12b37e7adc8606d690
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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