Sodium Bicarbonate → Methyl 3-(Aminomethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate

HRID 592957Notes

Reaction equation

HRID 592957 reaction equation
CC(C)(S([NH:6][CH2:7][C:8]1[N:16]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:10][C:9]=1[C:17]([O:19][CH3:20])=[O:18])=O)C.Cl.C(OCC)C.C([O-])(O)=O.[Na+]>ClCCl>[NH2:6][CH2:7][C:8]1[N:16]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:10][C:9]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10953452Ether hydrochlorideHCID 86684449Methyl 3-((1,1-Dimethylethylsulfinamido)methyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate

Product 1

HCID 86684450Methyl 3-(Aminomethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 238b (3.5 g, 11.2 mmol), saturated HCl/diethyl ether solution (15 mL), and dichloromethane (15 mL). The mixture was stirred at room temperature for 4 h. After the reaction was completed, saturated aqueous NaHCO3 solution (50 mL) was added to the reaction mixture and the mixture was extracted with dichloromethane (3×50 mL). The combined organic layer was evaporated under reduced pressure to afford 238c (2.2 g, 94%), which was directly used in the next step without further purification. MS: [M-NH2]+ 192.1. 1H NMR (500 MHz, MeOD) δ 6.28 (s, 1H), 4.38 (s, 2H), 4.03 (t, J=6.5 Hz, 2H), 3.84 (s, 3H), 2.78 (t, J=6.5 Hz, 2H), 2.06-2.02 (m, 2H), 1.87-1.82 (m, 2H).

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  3. customThe combined organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-43c1ed9843554e578b4f67d91f0226b6
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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