4,7-Diazaspiro[2.5]octane-4-carboxylic acid, 7-(3-oxetanyl)-, phenylmethyl ester → HCID 59605226, compound

HRID 1922715Notes

Reaction equation

HRID 1922715 reaction equation
C(OC([N:11]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:22][O:21][CH2:20]2)[CH2:15][C:12]21[CH2:14][CH2:13]2)=O)C1C=CC=CC=1>[Pd]>[O:21]1[CH2:22][CH:19]([N:16]2[CH2:15][C:12]3([CH2:13][CH2:14]3)[NH:11][CH2:18][CH2:17]2)[CH2:20]1

Participants

3

Reactant 1

HCID 596059144,7-Diazaspiro[2.5]octane-4-carboxylic acid, 7-(3-oxetanyl)-, phenylmethyl ester

Product 1

HCID 59605226HCID 59605226, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 7-oxetan-3-yl-4,7-diazaspiro[2.5]octane-4-carboxylic acid benzyl ester in IMS (3 mL) was added 10% Pd/C (60 mg) and the resulting mixture stirred under an atmosphere of H2 at r.t. for 20 h. The reaction mixture was filtered through Celite® and the filtrate loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH affording the title compound (90 mg, 90%). 1H NMR (CDCl3, 400 MHz): δ 4.63-4.63 (2H, m), 3.50-3.42 (2H, m), 3.00-2.98 (2H, m), 2.35-2.25 (2H, m), 2.15 (2H, s), 2.05-2.03 (2H, m), 0.68-0.63 (2H, m), 0.52-0.51 (2H, m)

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washwas washed with MeOH
  3. washthe product eluted with 2M NH3/MeOH affording the title compound (90 mg, 90%)

Sources & evidence

ORD record
ord-1feab03bfa124e918db82b7ee422b7a2
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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