Sodium bis(2-methoxyethoxy)aluminiumhydride → 6-Bromospiro[indoline-3,3'-thietane]

HRID 1618784Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=O)[C:10]3([CH2:13][S:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:13][S:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-bromospiro[indoline-3,3′-thietan]-2-one (0.260 g, 0.962 mmol) in toluene (39 mL) was added sodium bis(2-methoxyethoxy)aluminium hydride (60% in toluene, 1.47 mL, 4.81 mmol) dropwise under an atmosphere of argon gas. The solution was stirred at 80° C. for 40 min, cooled in an ice bath, quenched with aqueous 2N NaOH and treated with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] as a tan solid. Mass Spectrum (ESI) m/e=256.0 [(M+1) (79Br)] and 258.0 [(M+1) (81Br)].

Workup

temperaturecooled in an ice bath
customquenched with aqueous 2N NaOH
additiontreated with EtOAc
dry with materialThe combined organic extracts were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2f7db00f977c44109892726a27f1375f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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