HCID 66669391, compound → HCID 45116030, compound

HRID 244538Notes

Reaction equation

HRID 244538 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:14][C:15]([O:17]CC1C=CC=CC=1)=O)[CH2:4][N:5]1[CH2:13][CH2:12][CH2:11][C@H:6]1C(OC)=O.[H][H]>CO.[Pd]>[OH:1][CH2:2][C@@H:3]1[CH2:4][N:5]2[CH2:13][CH2:12][CH2:11][C@H:6]2[C:15](=[O:17])[NH:14]1

Participants

5

Reactant 2

HCID 66669391HCID 66669391, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 45116030HCID 45116030, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of methyl 1-[(2S)-3-hydroxy-2-({[(phenylmethyl)oxy]carbonyl}amino)propyl]-L-prolinate (3.50 g, 10.4 mmol) in methanol was added to 5% palladium on carbon (50 wt. % in water) in methanol and treated with hydrogen at 40 psi for 1 h. The mixture was filtered and the filtrate was brought to reflux briefly and then cooled and concentrated in vacuo to afford (3S,8aS)-3-(hydroxymethyl)hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one as a colorless solid (1.50 g, 8.83 mmol, 85% yield). 1H NMR (400 MHz, CDCl3): 7.28-7.22 (m, 1H), 3.83-3.75 (m, 1H), 3.69 (dd, 1H), 3.56 (dd, 1H), 3.31 (t, 1H), 3.08 (dd, 1H), 2.92 (dt, 1H), 2.76-2.70 (m, 1H), 2.66 (dd, 1H), 2.28-2.16 (m, 1H), 2.02-1.73 (m, 3H); MS (EI) for C8H14N2O2: 171 (MH+).

Workup

  1. filtrationThe mixture was filtered
  2. temperatureto reflux briefly
  3. temperaturecooled
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dee9b14e71f4696a55160a9b199f823
Source dataset
uspto-grants-2014_02
Patent number
US08658654B2

Reaction notes

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