Pivalaldehyde → HCID 66590719, compound

HRID 2363590Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([S:9]([N:12]2[CH2:16][C@H:15]3[C@H:17]([NH2:20])[CH2:18][CH2:19][C@H:14]3[CH2:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(=O)C(C)(C)C>>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:20][C@@H:17]2[C@@H:15]3[C@@H:14]([CH2:13][N:12]([S:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=4)(=[O:10])=[O:11])[CH2:16]3)[CH2:19][CH2:18]2)=[CH:26][CH:25]=1

Participants

Reactant 3

HCID 12417Pivalaldehyde

HCID 680234-Fluorobenzaldehyde

HCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590719HCID 66590719, compound

Procedure

The title compound was prepared by substituting (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step D of Example 252 for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine and 4-fluorobenzaldehyde for pivalaldehyde in the procedure described in Example 281: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.39-8.40 (bs, 1H), 8.22-8.24 (m, 1H), 7.93-7.95 (m, 1H), 7.75 (t, J=7.8 Hz, 1H), 7.41 (dd, J=8.3, 5.5 Hz, 2H), 7.13 (t, J=8.7 Hz, 2H), 3.71 (d, J=13.3 Hz, 1H), 3.67 (d, J=13.2 Hz, 1H), 3.39 (dd, J=9.8, 3.1 Hz, 1H), 3.16 (dd, J=9.6, 3.0 Hz, 1H), 3.06 (dd, J=9.8, 8.0 Hz, 1H), 2.96 (dd, J=9.6, 7.6 Hz, 1H), 2.85 (q, J=6.1 Hz, 1H), 2.47-2.56 (m, 1H), 2.30-2.35 (m, 1H), 1.93-2.07 (m, 1H), 1.87-1.94 (m, 1H), 1.79-1.87 (m, 1H), 1.29-1.38 (m, 1H), 1.20-1.29 (m, 1H); MS (ESI+) m/z 443 (M+H)+.

Sources & evidence

ORD record: ord-5e575f6b678d4feaa7e9285c0aff456c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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