tert-butyl [3-(cyclopropylmethyl)-2-oxo-2,3,4,7-tetrahydro-1H-1,3-diazepin-1-yl]acetate → tert-Butyl [3-(cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetate

HRID 1442871Notes

Reaction equation

HRID 1442871 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:11][CH:10]=[CH:9][CH2:8][N:7]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:6]2=[O:20])[CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([CH2:4][N:5]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([CH2:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[C:6]2=[O:20])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86606172tert-butyl [3-(cyclopropylmethyl)-2-oxo-2,3,4,7-tetrahydro-1H-1,3-diazepin-1-yl]acetate

Product 1

HCID 86606171tert-Butyl [3-(cyclopropylmethyl)-2-oxo-1,3-diazepan-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl [3-cyclopropylmethyl)-2-oxo-2,3,4,7-tetrahydro-1H-1,3-diazepin-1-yl]acetate from Step C (250 mg, 0.89 mmol) in EtOH (10 mL) was added 10% Pd/C (9.5 mg) and the reaction stirred vigorously under hydrogen (ca. 1 atm). After 90 min, the catalyst was filtered off and the filtrate was concentrated to yield the title compound. MS: m/z=283 (M+1).

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4bedbf49133144a5bc1bfec6f069024e
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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