cis-1-Benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine → Cis-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine

HRID 1954625Notes

Reaction equation

HRID 1954625 reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:14]2)[C@H:10]([CH2:24][OH:25])[CH2:9]1)C1C=CC=CC=1>CO.[C].[Pd]>[C:20]([O:19][C:17]([NH:16][C:13]1([C@H:11]2[CH2:12][NH:8][CH2:9][C@H:10]2[CH2:24][OH:25])[CH2:14][CH2:15]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 69563790cis-1-Benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine

Product 1

HCID 69563224Cis-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidineYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

cis-1-Benzyl-4-(1-tert-butoxycarbonylaminocyclopropyl)-3-hydroxymethylpyrrolidine (820.1 mg, 2.376 mmol) was dissolved in methanol (50 ml). After adding a 5% palladium-carbon catalyst (moisture content: 55.6%, 750 mg), the mixture was stirred under elevated hydrogen pressure (4.5 kg/cm2) over a period of one day and night. After filtering off the catalyst through celite (washed with methanol), the filtrate was concentrated under reduced pressure to obtain 578.8 mg (91.0%) of the titlle compound as a white amorphous substance.

Workup

  1. filtrationAfter filtering off the catalyst
  2. washthrough celite (washed with methanol)
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a2d055362c6d4aa48ae9286557340e69
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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