Morpholine → HCID 178453984, compound

HRID 1518853Notes

Reaction equation

HRID 1518853 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1.[BH4-].[Na+].O1CCN([C@H]2CC[C@H](NC(=O)[O-])CC2)CC1>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CO>[O:4]1[CH2:5][CH2:6][N:1]([C@@H:8]2[CH2:9][CH2:10][C@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:12][CH2:13]2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 4311764Sodium borohydrideHCID 178526092HCID 178526092, compound

Product 1

HCID 178453984HCID 178453984, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11026Titanium isopropoxideSolvent

Procedure

To a mixture of morpholine (4.08 ml) and tert-butyl 4-oxocyclohexylcarbamate (10 g) stirred for 24 hours at room temperature in titanium(IV) isopropoxide (27.5 ml), methanol (10 ml) was added followed by careful addition of sodium borohydride (3.55 g). The reaction mixture was quenched with water, extracted with ether (2×100 mL), dried over magnesium sulfate, filtered and concentrated. The crude product was purified by FC (silica gel 200 g, 30%-100% acetone/hexanes) providing two products, the title compound and trans 4-morpholinocyclohexylcarbamate.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ether (2×100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by FC (silica gel 200 g, 30%-100% acetone/hexanes)
  7. customproviding two products

Sources & evidence

ORD record
ord-2a2d3bea0d1e493d998b2b56f566bf1d
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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