Ammonia → 2-(2-cyclopentyl-1,3-dioxolan-2-yl)-N'-hydroxyacetimidamide

HRID 631436Notes

Reaction equation

HRID 631436 reaction equation
[CH:1]1([C:6]2([CH2:11][C:12]#[N:13])[O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:15][OH:16].N>>[CH:1]1([C:6]2([CH2:11][C:12](=[N:15][OH:16])[NH2:13])[O:10][CH2:9][CH2:8][O:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 443297Hydroxyamine hydrochlorideHCID 668766282-(2-Cyclopentyl-1,3-dioxolan-2-yl)acetonitrile

Product 1

HCID 866535152-(2-cyclopentyl-1,3-dioxolan-2-yl)-N'-hydroxyacetimidamide

Procedure

According to the procedure described in Example 133A Step 3, 2-(2-cyclopentyl-1,3-dioxolan-2-yl)acetonitrile (1.5 g, 8.3 mmol) was reacted with hydroxylamine hydrochloride (3.17 g, 45.5 mmol) and liquid ammonia (7.8 mL, 7N in methanol), to afford 2-(2-cyclopentyl-1,3-dioxolan-2-yl)-N′-hydroxyacetimidamide, which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 5.11 (bs, 2H), 4.20-3.95 (m, 4H), 2.38 (s, 2H), 2.33-2.22 (m, 1H), 1.73-1.41 (m, 8H); LC-MS (ESI) m/z 215 (M+H)+

Sources & evidence

ORD record
ord-df024ec49130456da0ff9d8738672754
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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