2-Amino-2-methyl-1-propanol → Tert-butyl 2-(1-hydroxy-2-methylpropan-2-yl)hydrazine-1-carboxylate

HRID 12913

Reaction equation

HRID 12913 reaction equation
[C:1]([O:5][C:6]([N:8]1C(C2C=CC(C#N)=CC=2)O1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22]>C(OCC)C>[C:1]([O:5][C:6]([NH:8][NH:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 2725038N-Boc-3-(4-cyanophenyl)oxaziridine

Product 1

HCID 54541694Tert-butyl 2-(1-hydroxy-2-methylpropan-2-yl)hydrazine-1-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of N-(tert-butoxycarbonyl)-3-(4-cyanophenyl)-oxaziridine (CAS #: 150884-56-3, purchased from Acros, 5.17 g, 21 mmol) in anhydrous diethyl ether (20 mL) was added to a solution of 2-amino-2-methyl-propan-1-ol (1.78 g, 20 mmol) in anhydrous diethyl ether (20 mL) at room temperature. The reaction mixture stirred at room temperature for 2 hours. Diethyl ether was evaporated under reduced pressure and the residue was purified by flash chromatography eluting with a gradient of 3-5% methanol/dichloromethane to give N′-(2-hydroxy-1,1-dimethyl-ethyl)-hydrazinecarboxylic acid tert-butyl ester (1.63 g, 40%) which was used without further purification.

Workup

  1. customDiethyl ether was evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography
  3. washeluting with a gradient of 3-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-279d0f43f58a4171a279e21137b58bb2
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Linked notes

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