Triphenylphosphine → t-Butyl 1,4-dioxepan-6-yl(1,3-dioxoisoindolin-2-yl)carbamate

HRID 1043881Notes

Reaction equation

CCOC(/N=N/C(OCC)=O)=O.[O:13]1[CH2:19][CH:18](O)[CH2:17][O:16][CH2:15][CH2:14]1.[O:21]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:31])[N:23]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:16]1[CH2:17][CH:18]([N:32]([N:23]2[C:22](=[O:21])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:31])[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:19][O:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

DEAD (2.2 M in toluen, 1.55 mL) was added dropwise to a solution of 1,4-dioxepan-6-ol (265 mg), t-butyl (1,3-dioxoisoindolin-2-yl)carbamate (560 mg) obtained in preparation example 14-(1) and triphenylphosphine (840 mg) in THF (10 mL) under ice-cooling over 3 minutes. The reaction mixture was stirred at 0° C. for 6 minutes, and further stirred at room temperature overnight The reaction mixture was concentrated under reduced pressure. After toluene (2.5 mL) was added to the resulting residue, the precipitated solid was removed by filtration. The filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%) to give the title compound (713 mg).

Workup

stirringfurther stirred at room temperature overnight The reaction mixture
concentrationwas concentrated under reduced pressure
additionAfter toluene (2.5 mL) was added to the resulting residue
customthe precipitated solid was removed by filtration
customThe filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 20%)

Sources & evidence

ORD record: ord-162a82999b05489ba8145a325ecca1d5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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