1-Butanol → HCID 9881978, compound

HRID 1700819Notes

Reaction equation

[C:1]1(=[CH:7][CH:8]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]1([S:16]([C:19]#[N:20])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(OCCCC)(OCCCC)OCCCC.C(O)CCC>C1(C)C=CC=CC=1>[C:10]1([S:16]([C:19]2[C:2]3[CH2:3][CH2:4][CH2:5][CH2:6][C:1]=3[CH:7]=[CH:8][N:20]=2)(=[O:17])=[O:18])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

First, 106 mg (purity of 84%, 0.72 mmol) of cyclohexylidene acetaldehyde, 120 mg (0.72 mmol) of benzenesulfonyl cyanide, 17 mg (0.072 mmol) of tributyl borate, 11 mg (0.14 mmol) of 1-butanol, and molecular sieves 4A (310 mg) as dehydrator were introduced to a flask (5 ml volume). Toluene (1.5 ml) was added as the solvent, and the mixture was heated for 14 hours at an internal temperature of 110° C. After this solution was cooled to room temperature, the molecular sieves was filtered off and the low-boiling components, such as solvent, etc., were removed under reduced pressure to give the desired, crude product. The crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/3) to give 31 mg of 1-benzenesulfonyl-5,6,7,8-tetrahydroisoquinoline with the following properties as yellow crystals (yield of 16% based on benzenesulfonyl cyanide).

Workup

temperatureAfter this solution was cooled to room temperature
filtrationthe molecular sieves was filtered off
customthe low-boiling components, such as solvent, etc., were removed under reduced pressure
customto give the
customThe crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record: ord-4377b2aa3fd846248fb9a50ebcd43cac
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350876B2

Reaction notes

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