Triethylamine → (Z)-butoxyimino-[(2S)-2-[[(3S)-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxycarbonyl]pyrrolidin-1-yl]-oxidoazanium

HRID 388214Notes

Reaction equation

HRID 388214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]3[CH:13]=[N:14][C:15]([CH3:18])=[C:16]([OH:17])[C:11]=3[CH2:10][O:9]2)=[CH:4][CH:3]=1.[CH2:19]([O:23]/[N:24]=[N+:25](/[N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29](O)=[O:30])\[O-:26])[CH2:20][CH2:21][CH3:22].C(N(CC)CC)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>C(Cl)Cl>[CH2:19]([O:23]/[N:24]=[N+:25](/[N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([O:17][C:16]1[C:11]2[CH2:10][O:9][C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:12]=2[CH:13]=[N:14][C:15]=1[CH3:18])=[O:30])\[O-:26])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 11680500Cicletanine, (S)-HCID 87274658(Z)-butoxyimino-[(2S)-2-carboxypyrrolidin-1-yl]-oxidoazanium

Product 1

HCID 88851090(Z)-butoxyimino-[(2S)-2-[[(3S)-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxycarbonyl]pyrrolidin-1-yl]-oxidoazanium

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridine-7-ol (346 mg, 1.32 mmol), 1-[(Z)-butoxy-NNO-azoxy]-L-proline (306 mg, 1.32 mmol), and triethylamine (369 mL, 2.65 mmol) in CH2Cl2 (10 mL) was added BOP-Cl (438 mg, 1.72 mmol). After stirring at rt over night, the mixture was purified by flash chromatography (Biotage 40+M) using 40-50% EtOAc/hexane gradient, affording the title compound: 1H NMR (500 MHz, CDCl3) δ 8.05 (s, 1H), 7.35-7.33 (m, 2H), 7.28-7.25 (m, 2H), 6.19 (s, 1H), 5.21 (dd, J=2.4, 14.1 Hz, 1H), 5.07 (dd, J=1.9, 14.2 Hz, 1H), 4.78 (dd, J=4.5, 14.1 Hz, 1H), 4.20 (t, 6.7 Hz, 2H), 3.93-3.88 (m, 1H), 3.73-3.68 (m, 1H), 2.54-2.48 (m, 1H), 2.47 (s, 3H), 2.26-2.15 (m, 3H), 1.76-1.70 (m, 2H), 1.45-1.38 (m, 2H), 0.93 (t, J=7.4 Hz, 3H).

Workup

  1. customthe mixture was purified by flash chromatography (Biotage 40+M)

Sources & evidence

ORD record
ord-220066fc1ce34958b38efccbbe37e543
Source dataset
uspto-grants-2013_02
Patent number
US08377911B2

Reaction notes

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