Water → HCID 178484843, compound

HRID 1063620Notes

Reaction equation

HRID 1063620 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

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 over a period of 6 h via a cannula keeping the temperature between 5-10° C. The reaction mixture was refluxed over night, and a mixture of Na2SO4, silica gel and water (160 g, 50 g, 80 mL) was added. The suspension was stirred for additional 30 min, filtered and concentrated. The crude material was titurated 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 mixture was refluxed over night
  4. additionwas added
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba52c4d8e39d4c17a532ebf414aeaf2c
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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