Hydrazine hydrate (1:1) → ((S)-1-Aminomethyl-butyl)-carbamic acid tert-butyl ester

HRID 882903Notes

Reaction equation

HRID 882903 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH2:12][N:13]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:9][CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].O.NN>CCO.C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH2:12][NH2:13])[CH2:9][CH2:10][CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66917015[(S)-1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 86651886((S)-1-Aminomethyl-butyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-butyl]-carbamic acid tert-butyl ester (2.80 g, 8.42 mmol) and hydrazine monohydrate (3.0 mL, 60.0 mmol) in EtOH (50 mL) and DCM (75 mL) is stirred at RT for 48 h. The precipitated solid is collected by filtration and washed with DCM to afford the crude product as a white solid that is used without further purification.

Workup

  1. filtrationThe precipitated solid is collected by filtration
  2. washwashed with DCM

Sources & evidence

ORD record
ord-8862f306594549be89bdcbf586b9862e
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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