Water → HCID 178521631, compound

HRID 1159405Notes

Reaction equation

HRID 1159405 reaction equation
[N:1]1([C:7]([CH:9]2[CH2:12][C:11](=[O:13])[CH2:10]2)=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[N:1]1([CH2:7][C@@H:9]2[CH2:12][C@H:11]([OH:13])[CH2:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 672785063-(Morpholin-4-ylcarbonyl)cyclobutanone

Product 1

HCID 178521631HCID 178521631, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of intermediate 39, 3-(Morpholin-4-ylcarbonyl)cyclobutanone (1.1 g, 6.1 mmol) in absolute THF (10 mL) was added dropwise to a solution of LiAlH4 (0.46 g, 12 mmol) in absolute THF (10 mL) in argon under stirring. The mixture was refluxed under stirring for 1 h, cooled, and 10 N NaOH (0.5 mL) and water (2.5 mL) were added. The organic layer was decanted, and the water layer was extracted with THF (2×5 mL). The organic layers were evaporated to give the title compound as colorless oil in ˜100% (1.1 g) yield. 1H-NMR (400 MHz)-data (dmso-d6): 4.8-4.95 (d, 1H, J=6.4 Hz, OH), 3.8 (ddddd, 4H, J=5.3 Hz, CHOH), 3.48-3.58 (m, 4H, CH2OCH2), 2.22-2.35 (m, 8H, (CH2)3N, cyclobutylCHH), 1.77-1.90 (m (ttt), 1H, CHCH2N), 1.36-1.47 (m, 2H, cyclobutylCHH).

Workup

  1. temperatureThe mixture was refluxed
  2. stirringunder stirring for 1 h
  3. temperaturecooled
  4. customThe organic layer was decanted
  5. extractionthe water layer was extracted with THF (2×5 mL)
  6. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-f9f0055cbc634f6d863407f6c0f82572
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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