Hydrazine hydrate (1:1) → tert-butyl N-(1-amino-4-methanesulfonylbutan-2-yl)carbamate

HRID 1504841Notes

Reaction equation

HRID 1504841 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17].O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86731712tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfonyl)butan-2-yl]carbamate

Product 1

HCID 86731713tert-butyl N-(1-amino-4-methanesulfonylbutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfonyl)butan-2-yl]carbamate (25 g, 63 mmol) in ethanol (500 mL) was added dropwise hydrazine hydrate (32 g, 0.63 mol) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes and then heated to reflux. After 2 hours, the reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel to give tert-butyl [1-amino-4-(methylsulfonyl)butan-2-yl]carbamate. MS ESI calc'd. for C10H23N2O4S [M+H]+ 267. found 267. 1H NMR (300 MHz, CD3OD) δ 3.59-3.54 (m, 1H), 3.29-3.09 (m, 2H), 2.96 (s, 3H), 2.71-2.56 (m, 2H), 2.08-1.76 (m, 2H), 1.45 (s, 9H).

Workup

  1. temperatureheated to reflux
  2. waitAfter 2 hours
  3. temperaturethe reaction mixture was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9b32206546ef424d8388dd56776a31ff
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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