1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl (4S)-4-(tritylamino)cyclopent-1-ene-1-carboxylate

HRID 1427330Notes

Reaction equation

[C:1]([NH:20][C@@H:21]1[CH2:25][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2>C(Cl)Cl>[C:1]([NH:20][C@@H:21]1[CH2:25][C:24]([C:26]([O:28][CH3:29])=[O:27])=[CH:23][CH2:22]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A reactor was charged with a solution of methyl (1S,4R)-4-(tritylamino)cyclopent-2-ene-1-carboxylate (4.75 kg, 12.4 mol) in methylene chloride. The reactor was charged with additional methylene chloride (15 L) to bring the total volume to 23.8 L. To the stirred solution was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.82 L, 32.2 mol). The reaction mixture was warmed to 40° C., with stirring for 16 to 22 h. 1H NMR (CDCl3) analysis of a small sample of the reaction mixture confirmed the formation of the product. The reaction was washed with 10% aqueous citric acid solution (2×7 L). The organic phase was concentrated under reduced pressure to afford the title compound as an oil. The oil was diluted with anhydrous toluene and concentrated to remove residual water and used without further purification. 1H NMR (300 MHz, CDCl3, δ): 7.60-7.54 (m, 5H), 7.34-7.17 (m, 10H), 6.53-6.50 (m, 1H), 3.70 (s, 3H), 3.50-3.40 (m, 1H), 2.60-2.52 (dd, J=16.6, 8.3 Hz, 1H), 2.24-2.20 (m, 1H), 2.16-2.05 (m, 1H) and 1.91-1.80 (m, 1H).

Workup

washThe reaction was washed with 10% aqueous citric acid solution (2×7 L)
concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record: ord-39abbc58b1274c61a248f9980b2521bf
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933225B2

Reaction notes

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