Hydrazine hydrate (1:1) → tert-Butyl (S)-(1-(aminooxy)propan-2-yl)carbamate

HRID 330926Notes

Reaction equation

HRID 330926 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].O.NN>C(O)C.C(Cl)Cl>[NH2:3][O:12][CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86693954tert-Butyl {(1S)-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]-1-methylethyl}carbamate

Product 1

HCID 39238211tert-Butyl (S)-(1-(aminooxy)propan-2-yl)carbamateYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {(1S)-2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]-1-methylethyl}carbamate 58 (1.2 g, 3.74 mmol) in a mixture of ethanol (3 mL) and DCM (20 mL) was added hydrazine hydrate (0.215 mL, 3.74 mmol). The reaction mixture was stirred at room temperature for 6 h. Precipitate was filtered off, the filtrate was evaporated and the residue was subjected to chromatography to give 59 (0.55 g, 77%) as a white solid.

Workup

  1. filtrationPrecipitate was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b0588f9874fb4144ac01dd945ecc0b39
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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