Water → HCID 178484843, compound

HRID 630374

Reaction equation

HRID 630374 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=O)OC(C)(C)C)[CH2:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1.C(Cl)(Cl)Cl>[CH3:15][NH:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([OH:7])[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178418329HCID 178418329, compound2×

Product 1

HCID 178484843HCID 178484843, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of lithium aluminium hydride (9 g, 0.23 mol) in tetrahydrofuran (425 mL) was added slowly tert-butyl (trans-4-hydroxycyclohexyl)carbamate (intermediate 1, 10 g, 0.046 mol). The mixture was refluxed overnight. Once the mixture was cooled to room temperature, 9 ml of water, 9 ml of 4N NaOH solution and 18 ml of water were carefully and successively dropped. The organic solvent was removed under reduced pressure and the crude obtained was dissolved with chloroform and dried over magnesium sulphate. The filtrate was evaporated to dryness and co evaporated with hexane to give the title compound as a white solid (89%). This intermediate is also described in JMC, 1987, 30(2), p 313.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. additionsuccessively dropped
  3. customThe organic solvent was removed under reduced pressure
  4. customthe crude obtained
  5. dry with materialdried over magnesium sulphate
  6. customThe filtrate was evaporated to dryness and co
  7. customevaporated with hexane

Sources & evidence

ORD record
ord-6778815796a845dda765468e30c93e3b
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Linked notes

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