phenylalaninol, (S)- → HCID 58237470, compound

HRID 885333Notes

Reaction equation

HRID 885333 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH:19]=O)[CH:6]=1.[NH2:22][C@@H:23]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:24][OH:25].C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:22][C@@H:23]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][OH:25])[CH:6]=1

Participants

6

Reactant 3

HCID 447213phenylalaninol, (S)-HCID 5003444Sodium cyanoborohydrideHCID 58237467[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58237470HCID 58237470, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester (0.166 g, 0.49 mmol), (S)-(−)-2-amino-3-phenyl-1-propanol (0.091 g, 0.6 mmol), sodium cyanoborohydride (0.062 g, 1.0 mmol), and acetic acid (1 drop) were combined in CH2Cl2 (10 mL) and stirred overnight at room temperature. After aqueous work-up, the crude material was used directly in the next step.

Sources & evidence

ORD record
ord-696c31059ef74e7c9441046225346d07
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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