Hydrazine hydrate (1:1) → tert-butyl N-[1-amino-3-(methylsulfanyl)propan-2-yl]carbamate

HRID 1504834Notes

Reaction equation

HRID 1504834 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:14][S:15][CH3:16].O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14][S:15][CH3:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 24720892tert-Butyl [2-phthalimido-1-(methylsulfanylmethyl)ethyl]carbamate

Product 1

HCID 72455593tert-butyl N-[1-amino-3-(methylsulfanyl)propan-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-(methylsulfanyl)propan-2-yl]carbamate (from Step 3 of PrepEx 4.11) (10.0 g, 28.6 mmol) in ethanol (150 mL) was added dropwise hydrazine hydrate (15.7 g, 286 mmol) at 0° C. and then 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 by chromatography on silica gel to give tert-butyl [1-amino-3-(methylsulfanyl)propan-2-yl]carbamate. MS ESI calc'd. for C9H21N2O2S [M+H]+ 221. found 221. 1H NMR (400 MHz, CD3OD) δ 3.66-3.63 (m, 1H), 2.83-2.79 (m, 1H), 2.64-2.50 (m, 3H), 2.12 (s, 3H), 1.45 (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 by chromatography on silica gel

Sources & evidence

ORD record
ord-b40620f37a934282a7b5552bd37843b5
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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