Ammonium formate → Azetidin-3-yl-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamicacid tert-butyl ester

HRID 2300209Notes

Reaction equation

HRID 2300209 reaction equation
[C:1]([O:5][C:6](=[O:44])[N:7]([CH:27]1[CH2:30][N:29](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:28]1)[CH2:8][C@H:9]([OH:26])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC=CC=2)=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6](=[O:44])[N:7]([CH:27]1[CH2:30][NH:29][CH2:28]1)[CH2:8][C@H:9]([OH:26])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12044732(1-Benzhydryl-azetidin-3-yl)-[(2S)-3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 12044733Azetidin-3-yl-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamicacid tert-butyl esterYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (1-Benzhydryl-azetidin-3-yl)-[(2S)-3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-carbamic acid tert-butyl ester (0.55 g, 0.9 mmol) in methanol (20 ml) was added ammonium formate (2.0 g, 30 mmol), and 0.2 g of 10% Pd/C. The mixture was stirred at reflux for 18 h. After cooling to room temperature, it was filtered through Celite. The solvent was evaporated to give 0.31 g of a beige solid; m.p. 130-134° C.; MS (ES) m/z 339.1 (MH+); HRMS (El) Calcd. for C37H42N2O5 (M+): 338.1841, Found: 338.1833.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationit was filtered through Celite
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d798a0167efa437baeb8d6f5c05a2bfa
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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