Morpholine → (R)-N-Boc-1-morpholino-2-propanamine

HRID 1670601Notes

Reaction equation

HRID 1670601 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:16])[CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH3:16])[CH2:10][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate

Product 1

HCID 57851166(R)-N-Boc-1-morpholino-2-propanamineYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heat a mixture of (R)-methanesulfonic acid 2-tert-butoxycarbonylamino-propyl ester (0.083 mol, 20 g) and morpholine (0.83 mol, 72.2 g) in acetonitrile (210 mL) to 65° C. for 16 h. Concentrate the reaction mixture, dilute the residue with water, extract with dichloromethane, combine organic layer and wash with water. Dry the organic layer over anhydrous sodium sulfate, filter and concentrate under vacuum to obtain the title compound (12 g, 62%) as yellow thick oil. 1H NMR (400 MHz, CDCl3) δ 1.13 (d, 3H), 1.43 (s, 9H), 2.21 (dd, 1H), 2.26-2.32 (m, 1H), 2.35-2.39 (m, 2H), 2.48-2.55 (m, 2H), 3.63-3.70 (m, 5H), 4.68 (br s, 1H, —NH).

Workup

  1. temperatureHeat
  2. concentrationConcentrate the reaction mixture
  3. additiondilute the residue with water
  4. extractionextract with dichloromethane
  5. washwash with water
  6. dry with materialDry the organic layer over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-cc610e987b104c01af76fa9e030e6186
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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