Hydrazine hydrate (1:1) → HCID 131734609, compound

HRID 595975Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:19]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.O.NN>C(O)C>[NH2:19][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:15])([CH3:14])[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)(methyl)carbamate (1.96 g, 4.72 mmol) in ethanol (15.75 mL) was added hydrazine hydrate (2.296 mL, 47.2 mmol). The reaction mixture was heated at 60° C. for 2 h. The reaction mixture was then filtered through Celite pad and the filtrate was concentrated. The residue was re-dissolved in ethanol and filtered through Celite® pad to remove extra white solid. NMR showed there was impurity in crude material. The crude product was filtered through a plug of silica, washed by DCM/EtOAc (2:1 ratio) and flashed with DCM/EtOAc (20% methanol, 0.5% NH3 in methanol) (1:1 ratio) to provide (s)-tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)(methyl)carbamate (1.2 g, 89% yield). LCMS (m/z): 285.1 (MH+), 0.65 min; 1H NMR (400 MHz, CDCl3) δ ppm 7.37 (s, 1H) 7.26 (3H), 4.20 (br. s., 1H), 2.85-2.77 (m, 3H), 1.51-1.38 (m, 9H).

Workup

filtrationThe reaction mixture was then filtered through Celite pad
concentrationthe filtrate was concentrated
dissolutionThe residue was re-dissolved in ethanol
filtrationfiltered through Celite® pad
customto remove extra white solid
filtrationThe crude product was filtered through a plug of silica
washwashed by DCM/EtOAc (2:1 ratio)

Sources & evidence

ORD record: ord-2ab0ecb4e6ce4c66bca9b5b47cbb6d5f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

Loading…