Water → HCID 68429571, compound

HRID 2191248Notes

Reaction equation

[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17](Cl)=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]([O-:24])([CH3:23])[CH3:22].[Na+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([O:24][C:21]([CH3:23])([CH3:22])[CH3:20])=[N:18][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-benzyl-8-chloro-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (1.0 g), tBuONa (0.70 g) and BINAP (0.068 g) in toluene (10 mL) was deaerated with an argon gas, Pd2(dba)3 (0.050 g) was added, and the resulting mixture was stirred at 100° C. for 2 hr under an argon atmosphere. The reaction solution was poured into water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane) to give 4-benzyl-8-tert-butoxy-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (0.81 g, 72%) as an colorless oil.

Workup

additionwas added
extractionthe resulting product was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
customdried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (solvent gradient; 0→40% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-01cc265d328f499e82e9725adcb8378d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329687B2

Reaction notes

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