Carbon Tetrachloride → methyl 4-(cis-1-tert-butoxycarbonyl-4-chloro-(2S)-pyrrolidinyl)methoxybenzoate

HRID 354397Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](O)[CH2:10][C@H:9]1[CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:46]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([Cl:46])[CH2:10][C@H:9]1[CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 4-(trans-1-tert-butoxycarbonyl-4-hydroxy-(2S)-pyrrolidinyl)methoxybenzoate (351 mg, 1.0 mmol) and Ph3P (393 mg, 1.5 mmol) in CHCl3 (5.0 ml) was added CCl4 (5.0 ml) at room temperature. The reaction mixture was stirred at 50° C. for 24 hr. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with n-hexane to n-hexane-EtOAc (4:1, v/v) as eluent to give methyl 4-(cis-1-tert-butoxycarbonyl-4-chloro-(2S)-pyrrolidinyl)methoxybenzoate (340 mg, 92%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.38-2.65 (m, 2H), 3.50-3.60 (m, 1H), 3.88 (s, 3H), 3.89-4.05 (m, 1H), 4.26-4.41 (m, 4H), 6.95-6.97 (m, 2H), 7.98 (d, J=8.5 Hz, 2H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by column chromatography on silica gel with n-hexane to n-hexane-EtOAc (4:1

Sources & evidence

ORD record: ord-7a8cf8a9379844f8816cc26fcabc3c77
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756378B2

Reaction notes

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