3-(Propan-2-yl)-1,2-oxazol-5-amine → 3-(Oxan-4-yl)-1,2-oxazol-5-amine

HRID 871449Notes

Reaction equation

HRID 871449 reaction equation
O=[C:2]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)[CH2:3][C:4]#[N:5].C(C1C=C(N)[O:17][N:16]=1)(C)C>>[O:9]1[CH2:10][CH2:11][CH:6]([C:2]2[CH:3]=[C:4]([NH2:5])[O:17][N:16]=2)[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 21152083-(Propan-2-yl)-1,2-oxazol-5-amineHCID 629075903-(Oxan-4-yl)-3-oxopropanenitrile

Product 1

HCID 592532673-(Oxan-4-yl)-1,2-oxazol-5-amineYield 44%

Procedure

Prepared from 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanenitrile (350 mg, 2.29 mmol) according to the method described for 3-isopropylisoxazol-5-amine in Example 122A Step 2, to afford 3-(tetrahydro-2H-pyran-4-yl)isoxazol-5-amine as a colorless solid (170 mg, 44%) which was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 5.01 (s, 1H), 4.40 (brs, 2H), 4.02-4.05 (m, 2H), 3.46-3.55 (m, 2H), 2.87 (m, 1H), 1.71-1.84 (m, 4H); LC-MS (ESI) m/z 169 (M+H)+.

Sources & evidence

ORD record
ord-dcac154d80b64daabb6440a23d8e2ab8
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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