5-Hydroxy-4,4-dimethyl-3-oxopentanenitrile → 2-(3-Amino-1,2-oxazol-5-yl)-2-methylpropan-1-ol

HRID 1917870Notes

Reaction equation

HRID 1917870 reaction equation
OCC(C)(C)C(=O)CC#N.C[O:12][CH2:13][C:14]([C:17]1[O:21][N:20]=[C:19]([NH2:22])[CH:18]=1)([CH3:16])[CH3:15]>>[NH2:22][C:19]1[CH:18]=[C:17]([C:14]([CH3:16])([CH3:15])[CH2:13][OH:12])[O:21][N:20]=1

Participants

3

Reactant 2

HCID 120447945-Hydroxy-4,4-dimethyl-3-oxopentanenitrileHCID 133396145-(1-Methoxy-2-methylpropan-2-yl)-1,2-oxazol-3-amine

Product 1

HCID 534063292-(3-Amino-1,2-oxazol-5-yl)-2-methylpropan-1-olYield 49%

Procedure

Prepared from 5-hydroxy-4,4-dimethyl-3-oxopentanenitrile (1 g, 7.90 mmol) according to the method described for 5-(1-methoxy-2-methylpropan-2-yl)isoxazol-3-amine. Purification via recrystallisation from diethyl ether afforded 2-(3-aminoisoxazol-5-yl)-2-methylpropan-1-ol as a colorless solid (600 mg, 49%). 1H NMR (300 MHz, CDCl3) δ 5.64 (s, 1H), 3.65 (s, 2H), 2.30 (brs, 2H), 1.31 (s, 6H).

Workup

  1. customPurification
  2. customvia recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-72337e34b175463b811cd53e7d873b79
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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