Water → HCID 57544575, compound

HRID 2355341Notes

Reaction equation

HRID 2355341 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([NH:11][C:12](=O)[C@@H:13]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:8][CH2:9][CH3:10].O.[OH-].[Na+]>C1COCC1>[C:24]([O:23][C:22]([NH:21][C@@H:13]([CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH2:12][NH:11][CH2:7][CH2:8][CH2:9][CH3:10])=[O:28])([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57544612HCID 57544612, compound

Product 1

HCID 57544575HCID 57544575, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1 M solution of LiAlH4 in THF (2.5 mL, 2.5 mmol) was added to a solution of (S)-tert-butyl 1-(butylamino)-3-cyclohexyl-1-oxopropan-2-ylcarbamate (384.7 mg, 1.18 mmol) in THF (10 mL) at 0° C. The reaction was permitted to warm to 25° C. and stirred for 12 h. The reaction was cooled to 0° C., and H2O (0.2 mL) and then 1 N NaOH (0.2 mL) were introduced with cautious dropwise addition maintaining the temperature below 10° C. The resulting gel was filtered through a pad of Celite and the solids were washed with Et2O (50 mL). The solvent was removed to yield crude (2S)-2-(tert-butoxycarbonylamino)-1-butylamino-3-cyclohexylpropane (312.8 mg, 85%) as a white solid. MS ESI+ve m/z 313 (M+1). The crude amine was used without further purification.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. temperaturemaintaining the temperature below 10° C
  3. filtrationThe resulting gel was filtered through a pad of Celite
  4. washthe solids were washed with Et2O (50 mL)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-00cabcae66724e0099fc992ec7858ef2
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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