Methanol → HCID 178453984, compound

HRID 2167967Notes

Reaction equation

HRID 2167967 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.CO.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:17]([O:16][C:15](=[O:21])[NH:14][C@H:11]1[CH2:10][CH2:9][C@@H:8]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:13][CH2:12]1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 8083MorpholineHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 4311764Sodium borohydride

Product 1

HCID 178453984HCID 178453984, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideSolvent

Procedure

To a solution of morpholine (4.08 g) 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/NaOH solution, extracted with ether, dried over magnesium sulfate, filtered, and concentrated. The product was separated from the trans isomer and purified by flash chromatography (silica gel, 50%-100% acetone in hexanes) to provide the title compound.

Workup

  1. customThe reaction mixture was quenched with water/NaOH solution
  2. extractionextracted with ether
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was separated from the trans isomer
  7. custompurified by flash chromatography (silica gel, 50%-100% acetone in hexanes)

Sources & evidence

ORD record
ord-88f29b907924404fbba2f213999a3ed3
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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