Hydroxyamine hydrochloride → HCID 178435056, compound

HRID 1821131Notes

Reaction equation

HRID 1821131 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1([CH3:17])[C@@H:7]2[CH2:8][C:9]3[C:13]([C@H:6]12)=[C:12]([CH3:14])[S:11][C:10]=3[C:15]#[N:16]>CO>[OH:3][NH:2][C:15]([C:10]1[S:11][C:12]([CH3:14])=[C:13]2[C:9]=1[CH2:8][C@H:7]1[C:5]([CH3:17])([CH3:4])[C@H:6]12)=[NH:16]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 57892441(1aS,5aR)-1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonitrile

Product 1

HCID 178435056HCID 178435056, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of K-tert.-butylate (281 mg, 2.5 mmol), hydroxylamine hydrochloride (208 mg, 3.0 mmol) in methanol (4 mL) is added (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopro-pa[a]pentalene-4-carbonitrile (203 mg, 1.0 mmol). The reaction mixture is stirred at rt for 5 h before it is filtered. The filtrate is purified by prep. HPLC (Water XTerrra Prep MS C18 30×75 mm, 10% to 95% acetonitrile in water containing 0.5% sat. aq. NH3) to give (1aS,5aR)-N-hydroxy-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxamidine (200 mg) as a colourless solid; LC-MS: tR=0.72 min, [M+1]+=237.09.

Workup

  1. filtrationis filtered
  2. customThe filtrate is purified by prep

Sources & evidence

ORD record
ord-acc5481698964ba2aba8baaa30e4688e
Source dataset
uspto-grants-2009_10
Patent number
US07605269B2

Reaction notes

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