(2R)-2-(Methoxymethyl)pyrrolidine → (R)-Methyl 4-((2-(methoxymethyl)pyrrolidin-1-yl)methyl)benzoate

HRID 1771078Notes

Reaction equation

HRID 1771078 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.N1([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)CCCC1>>[CH3:1][O:2][CH2:3][C@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 756589Methyl 4-(pyrrolidin-1-ylmethyl)benzoate

Product 1

HCID 68405623(R)-Methyl 4-((2-(methoxymethyl)pyrrolidin-1-yl)methyl)benzoate

Procedure

The title compound was synthesized from (R)-2-(methoxymethyl)pyrrolidine (0.175 g, 1.52 mmol) according to a procedure similar to that used for compound 56. 1H NMR (400 MHz, CDCl3): δ 7.98 (d, J=8.0 Hz, 2H), 7.41 (d, J=8.0 Hz, 2H), 4.16 (d, J=13.6 Hz, 1H), 3.91 (s, 3H), 3.42 (m, 2H), 3.33 (m, 4H), 2.92 (m, 1H), 2.73 (m, 1H), 2.19 (m, 1H), 1.93 (m, 1H), 1.70 (m, 3H). 13C NMR (100 MHz, CDCl3): δ 166.7, 144.7, 129.1, 128.4, 128.3, 76.0, 62.8, 58.9, 58.7, 54.2, 51.6, 28.0, 22.4. ESI-LRMS: [M+H]+=264 m/z.

Sources & evidence

ORD record
ord-5d0ae2113ce14e12987132994e20159e
Source dataset
uspto-grants-2016_02
Patent number
US09249087B2

Reaction notes

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