Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 1-(Prop-2-enyl)-3-(r)-(hydroxymethyl)-4-(s)-(3-thienyl)pyrrolidine

HRID 1386733Notes

Reaction equation

HRID 1386733 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[C:8]([OH:10])=O)=[CH:2]1.CO[CH2:13][N:14]([CH2:20][C:21]1C=CC=C[CH:22]=1)[CH2:15][Si](C)(C)C>>[CH2:20]([N:14]1[CH2:15][C@H:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[C@@H:7]([CH2:8][OH:10])[CH2:13]1)[CH:21]=[CH2:22]

Participants

3

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 735793(2E)-3-(3-Thienyl)-2-propenoic acid

Product 1

HCID 213410491-(Prop-2-enyl)-3-(r)-(hydroxymethyl)-4-(s)-(3-thienyl)pyrrolidine

Procedure

The title compound was prepared from trans-3-(3-thienyl)acrylic acid using procedures analogous to those described in EXAMPLE 1, Steps A-C, substituting N-methoxymethyl-N-trimethylsilylmethyl(prop-2-enyl)amine for N-methoxymethyl-N-trimethylsilylmethylbenzyl amine in Step B. For the title compound: 1H NMR (500 MHz) δ 2.30-2.34 (m, 1H), 2.44 (t, J=8.5, 1H), 2.67 (t, J=9.0, 1H), 2.77 (dd, J=5.0, 9.0, 1H), 3.02-3.15 (4H), 3.53 (dd, J=7.5, 10.0, 1H), 3.64 (dd, J=5.0, 10.0, 1H), 5.07 (d, J=10.0, 1H), 5.17 (d, J=17.5, 1H), 5.83-5.91 (m, 1H), 6.97-6.99 (2H), 7.20-7.22 (m, 1H); ESI-MS 224 (M+H).

Sources & evidence

ORD record
ord-c041b55fe4574ab49f5e4a1caf4367e2
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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