Ethanol → (S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine

HRID 378851Notes

Reaction equation

HRID 378851 reaction equation
C1(COC([NH:11][C@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[C:13]2=[O:27])=O)C=CC=CC=1.C(O)C.C([O-])=O.[NH4+]>[Pd].C1COCC1>[NH2:11][C@H:12]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([CH2:19][C:20]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[O:21])[C:13]1=[O:27]

Participants

6

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 598734911-[((3S)-3-[(phenylmethoxy)carbonyl]amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine

Product 1

HCID 12047820(S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidineYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 30° C. mixture of 1-[((3S)-3-[(phenylmethoxy)carbonyl]amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine (20 g, 54 mmol), ethanol (100 mL), THF (100 mL) and wet 10% Pd/C (4 g) was added ammonium formate (5.1 g, 81 mmol) over 45 min. After stirring for 3 h, the reaction was cooled to room temperature and filtered. The filtrate was concentrated, taken up in TBME (150 mL) and filtered again. The filtrate was concentrated in vacuo to provide 12.3 g (95%) of (S)-1-[(3-amino-hexahydro-2-oxo-1H-azepin-1-yl)acetyl]pyrrolidine.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. filtrationfiltered again
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-80262876905740c789ae69f1f18cc26a
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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