Ethanol → (1R,3S,6S)-tert-butyl-3-(aminomethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

HRID 705716Notes

Reaction equation

HRID 705716 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C>>[C:1]([O:5][C:6]([N:8]1[C@H:14]([CH2:15][NH2:16])[CH2:13][CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 117925141HCID 117925141, compound

Product 1

HCID 117925120(1R,3S,6S)-tert-butyl-3-(aminomethyl)-2-azabicyclo[4.1.0]heptane-2-carboxylate

Procedure

To a solution of D8 (11 g, 30.9 mmol) in ethanol (200 mL) hydrazine hydrate (7.28 mL, 150 mmol) was added and the mixture was stirred at room temperature for 16 hours. The precipitate was filtered off and the filtrate was concentrated. Then i-Pr2O was added, the precipitate was discarded and the filtrate was concentrated to give the title compound as yellow oil. Yield (6.7 g, 96%).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. additionThen i-Pr2O was added
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab98c9d760d04746be1e3a760b362260
Source dataset
uspto-grants-2015_11
Patent number
US09174977B2

Reaction notes

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