HCID 23635292, compound → tert-butyl (1R,5S)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylate

HRID 1816998Notes

Reaction equation

HRID 1816998 reaction equation
[C@@H:1]12[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:5]1[CH2:4][N:3](C(OCC1C=CC=CC=1)=O)[CH2:2]2>CO.[Pd]>[C@@H:1]12[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:5]1[CH2:4][NH:3][CH2:2]2

Participants

4

Reactant 1

HCID 23635292HCID 23635292, compound

Product 1

HCID 23635158tert-butyl (1R,5S)-3,6-diazabicyclo[3.2.0]heptane-6-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 38I (2.3 g, 6.92 mmol) in methanol (30 mL) was treated with 10% palladium on carbon (0.23 g) and stirred at room temperature under H2 (1 atm) for 10 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was concentrated to provide the title compound as a yellow oil. (1.27 g, 92% yield). 1H NMR (MeOH-d4, 300 MHz) δ 1.46 (s, 9H), 2.47 (dd, J=12.9, 3.7 Hz, 1H), 2.64 (dd, J=12.2, 5.7 Hz, 1H), 2.95 (m, 1H), 3.05 (d, J=12.2 Hz, 1H), 3.24 (d, J=12.5 Hz, 1H), 3.46 (m, 1H), 3.95 (m, 1H), 4.64 (dd, J=6.1, 3.8 Hz, 1H), MS (DCI/NH3) m/z 216 (M+NH4)+, 199 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0f7d23a0e3ea4e25a14dfbc29dce53a3
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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