Hydrazine hydrate (1:1) → tert-butyl N-(1-amino-3-methanesulfonylpropan-2-yl)carbamate

HRID 1504833Notes

Reaction equation

HRID 1504833 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16].O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:14][S:15]([CH3:18])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 76781197tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(methylsulfonyl)propan-2-yl]carbamate

Product 1

HCID 86731710tert-butyl N-(1-amino-3-methanesulfonylpropan-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)-3-(methylsulfonyl)propan-2-yl]carbamate (10.0 g, 26.2 mmol) in ethanol (150 mL) was added dropwise hydrazine hydrate (15.7 g, 262 mmol) at 0° C., and the reaction mixture was allowed to warm to ambient temperature. After 30 minutes, the reaction mixture was heated to reflux. After two hours, the reaction mixture was cooled, filtered, and concentrated under reduced pressure. The residue was purified via chromatography on silica gel to afford tert-butyl [1-amino-3-(methylsulfonyl)propan-2-yl]carbamate. MS ESI calc'd. for C9H21N2O4S [M+H]+ 253. found 253. 1H NMR (400 MHz, CD3OD) δ 4.06-4.00 (m, 1H), 3.30-3.27 (m, 2H), 3.00 (s, 3H), 2.82-2.69 (m, 2H), 1.44 (s, 9H).

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter two hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via chromatography on silica gel

Sources & evidence

ORD record
ord-8462c5014ba24a01bddf202d074ffc76
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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