Diethyl Ether → HCID 178513032, compound

HRID 2279489Notes

Reaction equation

HRID 2279489 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([OH:7])[CH2:3]1.CCN(C(C)C)C(C)C.Cl.[N:18]1([C:23](=N)[NH2:24])C=CC=N1.CCOCC>CN(C=O)C>[OH:7][C@H:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:23]([NH2:24])=[NH:18])[CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

Product 1

HCID 178513032HCID 178513032, compoundYield 164.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (1S,3S)-3-aminocyclopentanol (9.00 g, 89.0 mmol) (obtained from ASID pharmaceuticals) in DMF (45 mL) at RT under nitrogen was added DIPEA (31.0 mL, 178 mmol) followed by 1H-pyrazole-1-carboximidamide hydrochloride (14.7 g, 133 mmol). After stirring overnight Et2O (150 mL) was added and the reaction was stirred for 10 min. The Et2O was decanted and concentrated under high vacuum to afford 21 g (99%) of 1-((1S,3S)-3-hydroxycyclopentyl)guanidine (164) as a dark orange oil: MS m/z (APCI-pos) M+1=144.1

Workup

  1. additionwas added
  2. customThe Et2O was decanted
  3. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-0264c470e63540e2827f9900b363c7e1
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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