benzyl 4-((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-carbonyl)piperazine-1-carboxylate → ((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(piperazin-1-yl)methanone

HRID 1747140Notes

Reaction equation

HRID 1747140 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:17][C@H:13]3[O:14][CH2:15][CH2:16][C@@:12]3([C:18]([N:20]3[CH2:25][CH2:24][N:23](C(OCC4C=CC=CC=4)=O)[CH2:22][CH2:21]3)=[O:19])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9][C@@H:10]2[CH2:17][C@H:13]3[O:14][CH2:15][CH2:16][C@@:12]3([C:18]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)=[O:19])[CH2:11]2)[CH2:7][CH2:6][O:5][CH2:4]1

Participants

5

Reactant 2

HCID 86708144benzyl 4-((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-carbonyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86708146((3aS,5S,6aR)-5-(((3S,4S)-3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(piperazin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Step H (405 mg, 0.83 mmol, 1 eq) and 5% Pd/C (100 mg) in ethanol (10 mL) at rt was placed under a balloon of hydrogen gas overnight. The suspension was filtered through celite, washed with methanol, and the filtrates concentrated to give the product of Step I as a gum. Calculated for C18H31N3O4: 354.2 (M+1). found: 354.2.

Workup

  1. customat rt
  2. filtrationThe suspension was filtered through celite
  3. washwashed with methanol
  4. concentrationthe filtrates concentrated

Sources & evidence

ORD record
ord-0df2f072339444ef989eaf156b1eac6d
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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