HCID 68766780, compound → HCID 68767245, compound

HRID 1374375Notes

Reaction equation

HRID 1374375 reaction equation
C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][C@H:18]2[C:26]([O:28][CH3:29])=[O:27])[C:13]1=[O:30])=O)C1C=CC=CC=1>C(O)(C)C.[OH-].[Pd+2].[OH-]>[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:24])[CH3:25])[CH2:19][C@H:18]2[C:26]([O:28][CH3:29])=[O:27])[C:13]1=[O:30]

Participants

4

Reactant 1

HCID 68766780HCID 68766780, compound

Product 1

HCID 68767245HCID 68767245, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 3776IsopropanolSolvent2×

Procedure

20% Palladium hydroxide (0.30 g) was carefully wetted down under nitrogen with isopropanol (10 mL) then (3R,4S)-methyl 4-((3S)-3-(benzyloxycarbonylamino)-2-oxo-pyrrolidin-1-yl)-1-isopropylpiperidine-3-carboxylate (1.10 g) in isopropanol (10 mL) was added. The mixture was hydrogenated on a Parr shaker for 20 hours. Worked up by filtering off the catalyst under nitrogen through fiberglass filter paper. The filtrate was stripped to give (3R,4S)-methyl 4-((3S)-3-amino-2-oxopyrrolidin-1-yl)-1-isopropylpiperidine-3-carboxylate (695 mg) as an oil. Yield=93%. LCMS detects (M+H)+=284.34.

Workup

  1. filtrationby filtering off the catalyst under nitrogen through fiberglass
  2. filtrationfilter paper

Sources & evidence

ORD record
ord-7237adc9952d4480b18bcbb2e5c9bc31
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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