2,3-Dichlorobenzaldehyde → HCID 22115371, compound

HRID 1276362Notes

Reaction equation

HRID 1276362 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl:29][C:30]1[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:31]=1[CH:32]=O>ClC(Cl)C>[C:15]([O:19][C:20]([NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][N:26]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:37]([Cl:38])[C:30]=2[Cl:29])[CH2:25]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22115371HCID 22115371, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (3.2 g, 15 mmol, 1.5 equiv.) was added in one portion to a stirred solution of 3-(RS)-(N-tert-butoxycarbonylaminomethyl)pyrrolidine (2.0 g, 10 mmol) and 2,3-dichlorobenzaldehyde (1.9 g, 11 mmol, 1.1 equiv.) in dichloroethane (60 mL) at room temperature. The suspension was stirred overnight, then concentrated in vacuo. The residue was diluted with ether and quenched with 1 M hydrochloric acid. The aqueous phase was basified with 4 M sodium hydroxide to pH 12, then extracted with ethyl acetate. The organic extracts were combined and washed with brine, then dried over sodium sulfate and concentrated. Flash chromatography of the residue afforded 3-(RS)-(N-tert-butoxycarbonylaminomethyl)-1-(2,3-dichlorobenzyl)-pyrrolidine as a colorless oil (2.9 g). The oil was taken up into methylene chloride (30 mL) and treated with neat trifluoroacetic acid (5 mL). After 1 h, the volatile components were removed on a vacuum pump, then concentrated further under high vacuum to give 3-(RS)-aminomethyl-1-(2,3-dichlorobenzyl)pyrrolidine which was used directly without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ether
  3. customquenched with 1 M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-43145e0c7352449a9f857c714bbdad8f
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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