Propanal → HCID 86617382, compound

HRID 1435143Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH:19]=O.[CH:25](=O)[CH2:26][CH3:27].[C:29]([C@@H:32]([C@H:34]([C:36]([O-:38])=[O:37])[OH:35])[OH:33])([O-:31])=[O:30]>>[C:29]([C@@H:32]([C@H:34]([C:36]([OH:38])=[O:37])[OH:35])[OH:33])([OH:31])=[O:30].[CH2:25]([N:1]([CH2:2][C@@H:3]1[CH2:7][CH2:6][NH:5][CH2:4]1)[CH2:19][C:18]1[CH:17]=[C:16]([Cl:15])[CH:23]=[C:22]([Cl:24])[CH:21]=1)[CH2:26][CH3:27]

Participants

Reactant 4

HCID 527Propanal

HCID 357463,5-Dichlorobenzaldehyde

HCID 119400Tartrate

HCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86617382HCID 86617382, compound

Procedure

The title compound is prepared starting from (S)-3-(aminomethyl)-1-N-tert-butyloxycarbonylpyrrolidine following the procedures described in Example 11 except 3,5-dichlorobenzaldehyde replaces 2,4-dichlorobenzaldehyde in step (i) and propionaldehyde replaces acetone in step (ii). The L-tartrate salt is obtainable by freeze-drying from water-acetonitrile. 1H NMR (300 MHz, DMSO) δH: 7.47 (1H, s), 7.34 (2H, s), 3.83 (2H, s), 3.54 (2H, s), 3.27-3.21 (1H, m), 3.20-3.05 (2H, m), 2.76-2.70 (1H, m), 2.44-2.29 (5H, m), 2.08-1.85 (1H, m), 1.54-1.37 (3H, m), 0.82-0.78 (3H, m). LCMS: Rt=3.42 (12 min method) [M+H]=301/3.

Workup

dry with materialby freeze-drying from water-acetonitrile
customRt=3.42 (12 min method) [M+H]=301/3

Sources & evidence

ORD record: ord-37056156b440435d814d5b8fc0f593fa
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615648B2

Reaction notes

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