2-Naphthalenecarboxaldehyde → (S)-2-{[(Naphthalen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2220710Notes

Reaction equation

HRID 2220710 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH2:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH:26][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59772986(S)-2-{[(Naphthalen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl esterYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental conditions were analogous to Example 1. 0.27 g (1.76 mmol) of naphthalene-2-carbaldehyde, 0.35 g (1.76 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, were dissolved in 10 mL dichloromethane, and 0.55 g (2.64 mmol) of sodium triacetoxyborohydride was added. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using flash chromatography (ethyl acetate in hexane), yielded to 350 mg of the free base as colorless oil. LC-MSD, m/z for C21H28N2O2 [M+H]+: 341.2

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customThe residue from the organic layer was purified

Sources & evidence

ORD record
ord-e42a006ecdbc4501ba954f4b0b7963c0
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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