Sodium Hydroxide → 5-Chloro-6-methyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalene-2-carboxylic acid ethyl ester

HRID 1013357Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].C(NB)(C)(C)C.[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH2:27]O)=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12].[OH-].[Na+]>C(Cl)Cl>[CH2:11]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][C:20]3[C:26]([CH3:27])=[C:25]([Cl:29])[S:24][C:21]=32)[CH2:17]1)=[O:15])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Aluminum chloride (131.7 mg, 0.990 mmol) was added to a round bottom flask, cooled to 0° C. and diluted with anhydrous CH2Cl2 (3.3 ml). Next, tert-butylaminoborane (172 mg, 1.98 mmol) was added and the contents were stirred for 30 minutes. A solution of 5-Chloro-6-hydroxymethyl-3,3a,7,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[α]pentalene-2-carboxylic acid ethyl ester (99.7 mg, 0.33 mmol) in CH2Cl2 (330 μl) was added to the AlCl3/t-butylaminoborane complex. The reaction mixture slowly warmed to room temperature and stirred for 16 hours. Next, the contents were carefully poured into 15% NaOH and extracted with CH2Cl2 (2×50 ml). The organic layer was dried (MgSO4), solvent evaporated in vacuo, and the residue purified by preparative TLC (hexanes:EtOAc-7:3) to give the subtitle compound. MS calculated for C13H16ClNO2S +H 286, observed 286.

Workup

temperatureThe reaction mixture slowly warmed to room temperature
stirringstirred for 16 hours
extractionextracted with CH2Cl2 (2×50 ml)
dry with materialThe organic layer was dried (MgSO4), solvent
customevaporated in vacuo
customthe residue purified by preparative TLC (hexanes:EtOAc-7:3)

Sources & evidence

ORD record: ord-b6eab70175b14fa992ca9a2a46d403e1
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981919B2

Reaction notes

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