Sodium Carbonate → HCID 59178383, compound

HRID 386493Notes

Reaction equation

HRID 386493 reaction equation
[CH:1]1([CH:4]([NH2:8])[CH2:5][O:6][CH3:7])[CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl.O.O>[CH:1]1([CH:4]([NH:8][C:15](=[O:16])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:5][O:6][CH3:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 534149871-Cyclopropyl-2-methoxyethan-1-amine

Product 1

HCID 59178383HCID 59178383, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
17.5 °C

Procedure

Crude 1-cyclopropyl-2-methoxyethanamine from the previous step was dissolved in CH2Cl2/H2O (300 mL/300 mL) and Na2CO3 (111.9 g, 1.06 mol) was added. The reaction mixture was placed in an ice bath and CbzCl (16.46 g, 96.78 mmol) was added via syringe. During the addition, the internal reaction mixture temperature was maintained at 15-20° C. After the addition was complete, the reaction mixture was stirred at room temperature for 2 h. The mixture was poured into a separatory funnel, diluted with H2O, (300 mL), and extracted with CH2Cl2 (3×300 mL). The combined organic layers were washed with brine (300 mL), dried over MgSO4, filtered and concentrated. The product was purified by column chromatography on silica gel (30% ethyl acetate in hexanes) to furnish benzyl 1-cyclopropyl-2-methoxyethylcarbamate (17.2 g, 78% yield for 2 steps) as an oil which crystallized upon standing: mp 190.5-192° C.; 1H NMR (400 MHz, DMSO-d6) δ 7.39-7.29 (m, 5H), 7.17 (d, J=8.5 Hz, 1H), 5.00 (s, 2H), 3.36-3.34 (m, 2H), 3.23 (s, 3H), 3.19-3.14 (m, 1H), 0.85-0.79 (m, 1H), 0.43-0.37 (m, 1H), 0.35-0.22 (m, 2H), 0.20-0.16 (m, 1H); LRMS (ESI) mile 250.3 [(M+H)+, calcd for C14H20NO3 250.1].

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. additionDuring the addition
  3. additionAfter the addition
  4. additionThe mixture was poured into a separatory funnel
  5. extractionextracted with CH2Cl2 (3×300 mL)
  6. washThe combined organic layers were washed with brine (300 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromatography on silica gel (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-14826a4b6ea84dd188794572df1bb0b6
Source dataset
uspto-grants-2013_02
Patent number
US08372847B2

Reaction notes

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