HCID 86726719, compound → tert-Butyl [(3S,5R)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-5-methylpiperidin-3-yl]carbamate

HRID 1499490Notes

Reaction equation

HRID 1499490 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]3[O:17][CH2:18][CH2:19][C:9]=23)[CH2:5][C@@H:4]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3]1>CO.[Pd]>[NH2:14][C:13]1[C:8]([N:6]2[CH2:7][C@H:2]([CH3:1])[CH2:3][C@H:4]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:5]2)=[C:9]2[CH2:19][CH2:18][O:17][C:10]2=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 86726719HCID 86726719, compound

Product 1

HCID 86726720tert-Butyl [(3S,5R)-1-(5-amino-2,3-dihydrofuro[2,3-b]pyridin-4-yl)-5-methylpiperidin-3-yl]carbamateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [(3S,5R)-5-methyl-1-(5-nitro-2,3-dihydrofuro[2,3-b]pyridin-4-yl)piperidin-3-yl]carbamate (44.5 mg, 0.118 mmol) in MeOH (2.00 mL), 10 wt % Pd on carbon (9.3 mg, 0.0087 mmol) was added under a nitrogen atmosphere. The mixture was then hydrogenated (1 atm.) for 4 h. The reaction mixture was then filtered through a pad of diatomaceous earth (eluted with MeOH). The filtrate was concentrated under reduced pressure to give the crude product as a red semi-solid (41.0 mg). The crude product was used directly in the next step without further purification. LCMS calc. for C18H29N4O3 (M+H)+: m/z=349.2. found 349.2.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of diatomaceous earth (eluted with MeOH)
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d7e98a8c612f43aebf8c531b338a010d
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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