HCID 58537898, compound → HCID 58537924, compound

HRID 1473758Notes

Reaction equation

HRID 1473758 reaction equation
C([O:8][C:9]1[C:13]2([CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]2)[N:12]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:11](=[O:25])[C:10]=1[C:26]1[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][C:27]=1[CH3:34])C1C=CC=CC=1>CO.[Pd]>[CH:22]1([CH2:21][N:12]2[C:13]3([CH2:14][CH2:15][N:16]([O:19][CH3:20])[CH2:17][CH2:18]3)[C:9]([OH:8])=[C:10]([C:26]3[C:27]([CH3:34])=[CH:28][C:29]([CH3:33])=[CH:30][C:31]=3[CH3:32])[C:11]2=[O:25])[CH2:24][CH2:23]1

Participants

4

Reactant 1

HCID 58537898HCID 58537898, compound

Product 1

HCID 58537924HCID 58537924, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Debenzylation was conducted using an H-Cube® continuous-flow hydrogenator: 4-benzyloxy-1-cyclopropylmethyl-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (546 mg, 1.34 mmol) was dissolved in methanol (47 ml) and this substrate solution (0.029 M) pumped twice through a 5% Pd/C filled cartridge at a flow-rate of 1 mL/min, a temperature of 35° C. and a pressure of 2-3 bars. The collected product solution was concentrated, and the residue purified by chromatography on silica gel (ethyl acetate/heptane 1:1). Yield: 215 mg of 1-cyclopropylmethyl-4-hydroxy-8-methoxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound P2.8) as a white solid, mp 223-225° C.

Workup

  1. customa temperature of 35° C.
  2. concentrationThe collected product solution was concentrated
  3. customthe residue purified by chromatography on silica gel (ethyl acetate/heptane 1:1)

Sources & evidence

ORD record
ord-2ac2ef79018a4a75a06ca57ed73cb543
Source dataset
uspto-grants-2015_04
Patent number
US09018135B2

Reaction notes

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