Di-tert-butyl dicarbonate → [1-(3,4-Difluorophenyl)-2hydroxy-propyl]-carbamic acid-tert-butyl ester

HRID 1275213Notes

Reaction equation

HRID 1275213 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1)([OH:5])[CH3:4].[NH2:14][C:15]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)(C)[CH2:16][OH:17].[C:27](O[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(Cl)(Cl)Cl>[C:30]([O:29][C:27](=[O:28])[NH:1][CH2:2][C:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1)([OH:5])[CH3:4])([CH3:33])([CH3:32])[CH3:31].[C:38]([O:37][C:35](=[O:36])[NH:14][CH:15]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[CH:16]([OH:17])[CH3:2])([CH3:39])([CH3:40])[CH3:41]

Participants

6

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 229934451-Amino-2-(3,4-difluorophenyl)propan-2-olHCID 229934752-Amino-2-(3,4-difluorophenyl)propan-1-ol

Product 2

HCID 22048785[1-(3,4-Difluorophenyl)-2hydroxy-propyl]-carbamic acid-tert-butyl esterYield 60.1%HCID 22993544[2-(3,4-Difluorophenyl)-2-hydroxy-propyl]-carbamic acid-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1-amino-2-(3,4-difluorophenyl)-propan-2-ol and 2-amino-2-(3,4-difluorophenyl)-propan-1-ol (1.2 g, 6.4 mmol) in CHCl3 (50 mL) at 0° C. was added a solution of di-tert-butyl dicarbonate (1.74 g, 7.9 mmol) in CHCl3 (10 mL) in one portion and the resulting solution was stirred overnight at room temperature. The solvent was removed in vacuo and the residue was subjected to column chromatography on silica gel (2:1 hexane-EtOAc followed by EtOAc) to obtain [2-(3,4-difluorophenyl)-2-hydroxy-propyl]-carbamic acid-tert-butyl ester and [1-(3,4-Difluorophenyl)-2-hydroxy-propyl]-carbamic acid-tert-butyl ester as a white solid (1.1 g, 60.1%).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f0ad6b3f582c482db60deec4684dd688
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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