HCID 58743377, compound → HCID 58743394, compound

HRID 722826Notes

Reaction equation

HRID 722826 reaction equation
[N:1]([C@H:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@@H:5]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:6])=[N+]=[N-]>CO.[Pd]>[NH2:1][C@H:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@@H:5]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH3:6]

Participants

4

Reactant 1

HCID 58743377HCID 58743377, compound

Product 1

HCID 58743394HCID 58743394, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of azide 95 (25 mg, 0.06 mmol) in MeOH (1.5 mL) at room temperature, Pd—C (10% wt, 16 mg, 0.015 mmol) was added. The mixture was purged with a stream of dry Ar, and then H2. The reaction was stirred overnight under a H2 atmosphere (1 atm). The catalyst was filtered off through a 0.45 μm teflon filter in polypropylene housing, washing the filter with MeOH (15 mL) and the solvent was evaporated in vacuo to obtain amine 96 as a white solid (22 mg, 94% yield).

Workup

  1. customThe mixture was purged with a stream of dry Ar
  2. filtrationThe catalyst was filtered off through a 0.45 μm teflon
  3. filtrationfilter in polypropylene housing
  4. washwashing the
  5. filtrationfilter with MeOH (15 mL)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a2549baaf0384f3091e34b41e11aa439
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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