Sodium sulfate decahydrate → HCID 59383008, compound

HRID 1254325Notes

Reaction equation

HRID 1254325 reaction equation
[CH3:1][NH:2][C:3]([C@@H:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH2:9][CH2:8]1)=O.[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:5]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH2:9][CH2:8]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 tert-butyl (S)-1-(methylcarbamoyl)-2-(4-methylcyclohexyl)-ethylcarbamate (1.0075 g, 3.38 mmol, 1.0 equiv) in THF (40 mL) at 0° C. under N2 was added 1.0 M LiAlH4 in THF (7 mL, 7 mmol, 2.1 equiv). The mixture was stirred at rt for 19 h and 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 product (1.04 g) was used in the next step without further purification. LC-MS (3 min) tR=1.37 min, m/z 285 (MH+), 229.

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 product (1.04 g) was used in the next step without further purification
  6. customLC-MS (3 min) tR=1.37 min, m/z 285 (MH+), 229

Sources & evidence

ORD record
ord-039a0b2e906b45bc9b356b153315f75f
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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