3,5-Dichlorobenzaldehyde → HCID 86617381, compound

HRID 1435142Notes

Reaction equation

HRID 1435142 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.[C:25]([C@@H:28]([C@H:30]([C:32]([O-:34])=[O:33])[OH:31])[OH:29])([O-:27])=[O:26]>>[C:25]([C@@H:28]([C@H:30]([C:32]([OH:34])=[O:33])[OH:31])[OH:29])([OH:27])=[O:26].[CH3:25][CH:28]([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)[CH3:30]

Participants

4

Reactant 3

HCID 357463,5-DichlorobenzaldehydeHCID 119400TartrateHCID 1514454tert-Butyl (3S)-3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86617381HCID 86617381, 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). The L-tartrate salt is obtainable by freeze-drying from water-acetonitrile. 1H NMR (300 MHz, DMSO) δH: 7.45 (1H, s), 7.34 (2H, s), 3.88 (2H, s), 3.55 (2H, s), 3.22-3.01 (3H, m), 2.83-2.72 (2H, m), 2.37 (3H, brs), 1.98-1.91 (1H, m), 1.60-1.45 (1H, m), 0.97 (6H, m). LCMS: Rt=3.17 (12 min method) [M+H]=301/3.

Workup

  1. dry with materialby freeze-drying from water-acetonitrile
  2. customRt=3.17 (12 min method) [M+H]=301/3

Sources & evidence

ORD record
ord-77aaa58e8a6c412c8fbc87cc0ea5772f
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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