Benzyl [(9S)-11-oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetate → [(9S)-11-Oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetic acid

HRID 1367258Notes

Reaction equation

HRID 1367258 reaction equation
[O:1]=[C:2]1[C:8]2([CH2:12][CH2:11][CH2:10][CH2:9]2)[NH:7][CH2:6][CH2:5][C@@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]1[CH2:19][C:20]([O:22]CC1C=CC=CC=1)=[O:21]>CO.[Pd]>[O:1]=[C:2]1[C:8]2([CH2:9][CH2:10][CH2:11][CH2:12]2)[NH:7][CH2:6][CH2:5][C@@H:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]1[CH2:19][C:20]([OH:22])=[O:21]

Participants

4

Reactant 1

HCID 86616407Benzyl [(9S)-11-oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetate

Product 1

HCID 66973328[(9S)-11-Oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl [(9S)-11-oxo-9-phenyl-6,10-diazaspiro[4.6]undec-10-yl]acetate from Step B (0.190 g, 0.484 mmol) in methanol (10 mL) was passed through an H-Cube™ continuous flow hydrogenation reactor at 50 Bar of H2 using a Pd/C catalyst at ambient temperature. The solution was concentrated in vacuo to yield the title compound. MS: m/z=303 (M+1).

Workup

  1. customat ambient temperature
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7c75472f1a4d4d2d98e390f59bad3d57
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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