Ammonia → Octahydrocyclopenta[b]pyrrole-2-carboxylic acid

HRID 424342Notes

Reaction equation

HRID 424342 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=O)[C:3]([OH:5])=[O:4].O=C1CCCC1CC(NC(N)=O)C(O)=O.N.[H][H]>O.[Pd]>[NH:1]1[C@H:2]([C:3]([OH:5])=[O:4])[CH2:6][C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25262532HCID 25262532, compoundHCID 59471170HCID 59471170, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 194816Octahydrocyclopenta[b]pyrrole-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(S)-2-amino-3-(2-oxocyclopentyl)propanoic acid as obtained in Example 3 (130 mg, 0.76 mmol) was dissolved in water (2 mL) and the pH was adjusted to 9 with 25% aqueous NH3 solution. Then, 10% Pd/C (5 mg) was added and hydrogenation was performed under 5 bar of hydrogen gas for 16 h. At the end of the reaction, the catalyst was filtered off on a pad of celite under suction and the product (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid was isolated after evaporation of the water layer in vacuo at 80° C. Weight 118 mg. 100% yield. Diastereomeric excess >95% (determined by chiral HPLC). 1H NMR: (DMSO-d6, 300 MHz): δ 10.54 (br s, 1H), 8.71 (br s, 1H), 4.22 (dd, 1H), 3.98 (t, 1H), 2.86-2.76 (m, 1H), 2.49-2.42 (m, 1H), 2.00-1.96 (m, 1H), 1.80-1.40 (m, 6H).

Workup

  1. customAt the end of the reaction
  2. filtrationthe catalyst was filtered off on a pad of celite under suction

Sources & evidence

ORD record
ord-fcefa1920989418994b98e1ed285304a
Source dataset
uspto-grants-2012_01
Patent number
US08105807B2

Reaction notes

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