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

Participants

Role	Name	HCID	Charge
Reactant	Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine	HCID 353442	—
Reactant	Cinnamic Acid	HCID 444539	—
Reactant	(2E)-3-(3-Thienyl)-2-propenoic acid	HCID 735793	—
Reactant	N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amine	HCID 18374742	—
Reactant	((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol	HCID 21341047	—
Product	1-(Prop-2-enyl)-3-(r)-(hydroxymethyl)-4-(s)-(3-thienyl)pyrrolidine	HCID 21341049	—

Reaction Steps

The title compound was prepared using procedures analogous to those used to prepare 1-benzyl-3-(R)-(hydroxymethyl)-4-(S)-phenylpyrroldine (Pyrrolidine 1, Step C), except that trans-3-(3-thienyl)acrylic was substituted for trans-cinnamic acid in Step A and N-methoxymethyl-N-trimethylsilylmethyl(prop-2-enyl)amine was substituted for N-methoxymethyl-N-trimethylsilylmethyl benzyl 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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06498161B1
Source dataset	uspto-grants-2002_12
ORD ID	ord-c44204bc4f6148caaeeafc35f52c45a2
Source note	uspto-grants-2002_12