Thionyl Chloride → 5-Allyloxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride

HRID 1824416Notes

Reaction equation

HRID 1824416 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH:12]=[CH2:13])[N:6]1C(OC(C)(C)C)=O)=[O:4].S(Cl)([Cl:23])=O>CO>[ClH:23].[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH:12]=[CH2:13])[NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 695846015-Allyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 695844965-Allyloxy-pyrrolidine-2-carboxylic acid methyl ester hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-allyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, 4, (7.28 g, 27 mmol) in MeOH is added thionyl chloride (4 mL, 54 mmol). The solution is stirred overnight and the solvent removed in vacuo to afford 4.25 g (95% yield) of the desired product as a dark yellow crystal. 1H-NMR (300 MHz, CDCl3): δ 11.47 (s, 1H), 8.15 (s, 1H), 5.81 (m, 1H), 5.23 (m, 2H), 4.55 (s, 1H), 3.85 (s, 3H), 2.88 (m, 1H), 2.59–2.42 (m, 2H), 2.24 (m, 1H), 1.81 (m, 1H). 13C-NMR (75.5 MHz, CDCl3): δ 170.0, 132.7, 132.3, 120.2, 119.6, 60.6, 60.2, 59.4, 58.9, 53.9, 36.6, 29.5, 29.2, 28.3. ESI MS 170.13 (M+H).

Workup

  1. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-25146b4edb73476b8979191abba6eeb8
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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