Pyridine → (Z)-butoxyimino-[(2S)-2-(1-chloroethoxycarbonyloxymethyl)pyrrolidin-1-yl]-oxidoazanium

HRID 388216Notes

Reaction equation

HRID 388216 reaction equation
[CH2:1]([O:5]/[N:6]=[N+:7](/[N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[CH2:14][OH:15])\[O-:8])[CH2:2][CH2:3][CH3:4].Cl[C:17]([O:19][CH:20]([Cl:22])[CH3:21])=[O:18].N1C=CC=CC=1>C(Cl)Cl>[C:17](=[O:18])([O:19][CH:20]([Cl:22])[CH3:21])[O:15][CH2:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][N:9]1/[N+:7](/[O-:8])=[N:6]/[O:5][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 5213051-Chloroethyl chloroformateHCID 88851203(Z)-butoxyimino-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-oxidoazanium

Product 1

HCID 88851464(Z)-butoxyimino-[(2S)-2-(1-chloroethoxycarbonyloxymethyl)pyrrolidin-1-yl]-oxidoazanium

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(2S)-1-[(2)-butoxy-NNO-azoxy]pyrrolidin-2-yl}methanol (Example 1, Step A) (856 mg, 3.94 mmol) in CH2Cl2 (15 mL) at rt was added 1-chloroethyl chloroformate (676 mg, 4.73 mmol) and followed by pyridine (935 mg, 11.8 mmol). After stirring at rt for 3 h, the mixture was purified by flash chromatography (Biotage 25+M) using 10-30% EtOAc/hexane gradient, affording the title compound.

Workup

  1. customthe mixture was purified by flash chromatography (Biotage 25+M)

Sources & evidence

ORD record
ord-8ec564fdea094ad69bef23ae780b6785
Source dataset
uspto-grants-2013_02
Patent number
US08377911B2

Reaction notes

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