Sodium Hydroxide → HCID 178484831, compound

HRID 536322Notes

Reaction equation

HRID 536322 reaction equation
C(O[C:6](=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.O.[OH-].[Na+]>C1COCC1.O>[CH3:6][NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 178419079HCID 178419079, compound

Product 1

HCID 178484831HCID 178484831, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To the stirred solution of (trans)-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (4.29 g, 20.0 mmol) in THF (160 ml) (under argon atmosphere) was added LiAlH4 (3.13 g, 80 mmol) in three portions, at 0-5° C. The suspension was heated to 70° C. and stirred for additional 18 h. The reaction mixture was cooled to 0° C. and then subsequently addition of THF-H2O 1:1 (4 ml), 4M NaOH (8 ml) and water (12 ml). Stirring was continued for 3 h at RT. The white suspension was filtered (Celite) and the filtrate was concentrated in vacuo to get the crude title compound as a slightly yellow liquid. This material was used for the next step without further purifications.

Workup

  1. customat 0-5° C
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. stirringStirring
  4. waitwas continued for 3 h at RT
  5. filtrationThe white suspension was filtered (Celite)
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa8ec8410ba549ac944c4fb9f508efe4
Source dataset
uspto-grants-2014_10
Patent number
US08859586B2

Reaction notes

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