Water → HCID 178484843, compound

HRID 2118227Notes

Reaction equation

HRID 2118227 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:15](=O)[NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1)C1C=CC=CC=1.[O-]S([O-])(=O)=O.[Na+].[Na+].O>C1COCC1>[CH3:15][NH:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 178523817HCID 178523817, compound

Product 1

HCID 178484843HCID 178484843, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Over a period of 6 h to a suspension of 37.9 g (0.94 mol, 2.0 eq) of LAH in 1.3 L of THF was added a suspension of 117 g (0.47 mol) of trans-4-hydroxy-cyclohexylcarbamic acid benzyl ester in 1 L of THF via a cannula keeping the temperature between 5-10° C. The reaction was refluxed over night and a mixture of Na2SO4, silica gel and water (160 g, 50 g, 80 mL) was added, stirred for additional 30 min, filtered and concentrated. The crude material was triturated with n-hexane to yield 27.9 g (46%) of trans-4-methylamino-cyclohexanol. Column chromatography of the mother liquor on silica gel yielded additional 17.1 g (28%) of trans-4-methylamino-cyclohexanol as white solid, MS: 129 (MH+) [in analogy to: Venuti et al., J.Med.Chem. 30:303-318 (1987)].

Workup

  1. additionwas added
  2. custombetween 5-10° C
  3. temperatureThe reaction was refluxed over night
  4. additionwas added
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was triturated with n-hexane

Sources & evidence

ORD record
ord-9c4e7041178c44ec83fa0bceb2cc9c08
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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