Morpholine → HCID 178453984, compound

HRID 2168394Notes

Reaction equation

HRID 2168394 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-f72415005cc94d0b9949245874f22599
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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