Methanol → HCID 68711075, compound

HRID 451790Notes

Reaction equation

HRID 451790 reaction equation
[CH3:1][N:2]([CH2:12][C@@H:13]([NH:22]C(=O)OC(C)(C)C)[CH2:14][CH:15]1[CH2:20][CH2:19][CH:18](C)[CH2:17][CH2:16]1)[C:3]([O:5][CH2:6][CH2:7][Si:8]([CH3:11])([CH3:10])[CH3:9])=[O:4].[H][H].[CH3:32]O>[Pd]>[NH2:22][CH:13]([CH2:14][C:15]1([CH3:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH2:12][N:2]([CH3:1])[C:3](=[O:4])[O:5][CH2:6][CH2:7][Si:8]([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 68711192HCID 68711192, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68711075HCID 68711075, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 250 mL round bottom flask was charged with 0.2479 g (0.54 mmol) of (S)-tert-butyl 1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(4-methylcyclohexyl)propan-2-ylcarbamate, 0.2784 g of 10% Pd/C, and 20 mL of MeOH. The reaction mixture was stirred at rt under a balloon of hydrogen for 5 h. The mixture was then filtered through filter agent, Celite® 545, washed with MeOH. The filtrate was evaporated under reduced pressure to afford 0.1799 g (100%) of 2-(trimethylsilyl)ethyl 2-amino-3-(1-methylcyclohexyl)propyl(methyl)carbamate, which was used in the next step without further purification. MS ESI +ve m/z 329 (M+H).

Workup

  1. filtrationThe mixture was then filtered
  2. filtrationthrough filter agent, Celite® 545
  3. washwashed with MeOH
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68d667670d534672abd912520dc32733
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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