Oleic Acid → trans-1-(tert-Butoxycarbonyl)-3,4-bis(((Z)-octadec-9-enoyloxy)methyl)pyrrolidine

HRID 1479309Notes

Reaction equation

HRID 1479309 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][OH:14])[C@H:10]([CH2:15][OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([OH:36])(=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([CH2:15][O:16][C:17](=[O:36])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@H:11]([CH2:13][O:14][C:17](=[O:36])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 445639Oleic AcidHCID 59512458(3S,4S)-tert-Butyl 3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86682225trans-1-(tert-Butoxycarbonyl)-3,4-bis(((Z)-octadec-9-enoyloxy)methyl)pyrrolidine

Procedure

Compound XIII-1 (280 mg, 54.6%) was obtained in the same manner as that in Reference Example 2, by using trans-3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (156 mg, 0.674 mmol) obtained by using the method described in WO2006/100036 and oleic acid (Tokyo Chemical Industry Co., Ltd.; 419 mg, 1.48 mmol).

Workup

  1. customCompound XIII-1 (280 mg, 54.6%) was obtained in the same manner as that in Reference Example 2
  2. customobtained

Sources & evidence

ORD record
ord-c9d3143db1374717a4e7b112775fdb49
Source dataset
uspto-grants-2016_08
Patent number
US09408914B2

Reaction notes

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