Methylhydrazine → tert-Butyl (S)-3-(aminooxy)pyrrolidine-1-carboxylate

HRID 2264957Notes

Reaction equation

HRID 2264957 reaction equation
CNN.[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(Cl)Cl>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([O:16][NH2:17])[CH2:12]1)=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 59704735(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59596622tert-Butyl (S)-3-(aminooxy)pyrrolidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl hydrazine (0.23 mL, 4.40 mmol) was added dropwise over 5 minutes to a solution of (S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.43 g, 4.3 mmol) in DCM (12 mL). The mixture was stirred at ambient temperature for 1 hour then evaporated. The resultant residue was suspended in diethyl ether (10 mL) and the solid was filtered. The filtrate was concentrated to provide the title compound as a colourless oil (0.86 g, 99%). 1H NMR (CDCl3, 400 MHz) 4.24-4.26 (m, 1H), 3.60-3.66 (m, 1H), 3.44-3.54 (m, 1H), 3.30-3.42 (m, 2H), 2.03-2.12 (m, 1H), 1.84-1.96 (m, 1H), 1.46 (s, 9H).

Workup

  1. customthen evaporated
  2. filtrationthe solid was filtered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-44227e37a5ac4ffa8960d9acb3315523
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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