Sodium sulfate decahydrate → HCID 59383008, compound

HRID 451784Notes

Reaction equation

HRID 451784 reaction equation
[CH3:1][NH:2][C:3](=O)[C@@H:4]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH2:7]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][NH:2][CH2:3][C@@H:4]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([CH3:12])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59382925HCID 59382925, compound

Product 1

HCID 59383008HCID 59383008, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-tert-butyl 1-(methylamino)-3-(4-methylcyclohexyl)-1-oxopropan-2-ylcarbamate (1.0075 g, 3.38 mmol, 1.0 equiv) in THF (40 mL) was added 7 mL (7 mmol, 2.1 equiv) of 1.0 M LiAlH4 in THF at 0° C. under N2. The mixture was stirred at rt for 19 h and then sodium sulfate decahydrate (6.45 g, 20 mmol) was added carefully to quench excess LiAlH4. The mixture was filtered and the solid was washed with ether. After the solvents were removed in vacuo, the crude (S)-tert-butyl 1-(methylamino)-3-(4-methylcyclohexyl)propan-2-ylcarbamate (1.04 g) was used in the next step without further purification. MS ESI +ve m/z 285 (M+H).

Workup

  1. customto quench excess LiAlH4
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with ether
  4. customAfter the solvents were removed in vacuo
  5. customthe crude (S)-tert-butyl 1-(methylamino)-3-(4-methylcyclohexyl)propan-2-ylcarbamate (1.04 g) was used in the next step without further purification

Sources & evidence

ORD record
ord-159d1de5dfbc4efb8ebb9ca2f35ac850
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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