Morpholine → HCID 178453984, compound

HRID 629632Notes

Reaction equation

HRID 629632 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-b8d1e8c493074d1e80e75a23d8f78662
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

Loading…