Triethylamine → HCID 123911103, compound

HRID 2203667Notes

Reaction equation

HRID 2203667 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25](=O)[CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH:36]([NH:39][NH2:40])([CH3:38])[CH3:37].C(N(CC)CC)C>C(O)C>[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[N:39]([CH:36]([CH3:38])[CH3:37])[N:40]=[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:26]=2)[CH2:20]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855731-Isopropylhydrazine hydrochlorideHCID 124026306HCID 124026306, compound

Product 1

HCID 123911103HCID 123911103, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-2,4-dioxobutanoate (0.40 kg, 84 mmol) in ethanol (500 mL) was added N-isopropylhydrazine hydrochloride (9.7 g, 84 mmol) at room temperature. After 16 h, triethylamine was added, and the resulting mixture was concentrated in vacuo. Purification of the residue by flash column chromatography (9% ethyl acetate in petroleum ether) afforded ethyl 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1-isopropyl-1H-pyrazole-3-carboxylate (19.5 g, 45%) as a colorless oil. LRMS: [M+H]+=517.1.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customPurification of the residue by flash column chromatography (9% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-8037147869d7400f8abba70d8c8741b4
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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