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

HRID 2185525Notes

Reaction equation

HRID 2185525 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17]C=C[CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)[C:2]1C=CC=C[CH:3]=1.C1C(/C=C/C(O)=O)=C[S:23]C=1.C(O)(=O)/C=C/C1C=CC=CC=1.COCN(CC=C)C[Si](C)(C)C.COCN(CC1C=CC=CC=1)C[Si](C)(C)C>>[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][S:23][CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 444539Cinnamic AcidHCID 735793(2E)-3-(3-Thienyl)-2-propenoic acidHCID 18374742N-(methoxymethyl)-N-((trimethylsilyl)methyl)prop-2-en-1-amineHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

Product 1

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

Procedure

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) δ2.30-2.34 (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).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6e22a4ec846745158499f28d371866e2
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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