Ammonium formate → HCID 67151626, compound

HRID 1187773Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:17][CH:16]=2)[C@H:11]([CH3:35])[O:10][C:9]1([CH3:37])[CH3:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[C@H:11]([CH3:35])[O:10][C:9]1([CH3:36])[CH3:37])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (4S,5S)-4-{2-[4-(benzhydrylidene-amino)-phenyl]-ethyl}-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.23 g) in methanol (50 ml) was added ammonium formate (6.13 g). The reaction mixture was degassed by bubbling argon through the mixture for several minutes. 10% Pd/C (207 mg) was added and the reaction mixture was stirred at 60° C. for 1 hour. TLC showed the reaction was complete. The reaction mixture was filtered through celite and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, gradient: 0% to 100% EtOAc in hexane) to afford (4S,5S)-4-[2-(4-amino-phenyl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as a yellow oil (1.76 g, 81%). MS (ISP): 335.2 ([M+H), 235.2 ([M−C4H8—CO2]+).

Workup

customThe reaction mixture was degassed
customby bubbling argon through the mixture for several minutes
addition10% Pd/C (207 mg) was added
filtrationThe reaction mixture was filtered through celite and
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (silica gel, gradient: 0% to 100% EtOAc in hexane)

Sources & evidence

ORD record: ord-90843160497943409861805aa417dae1
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673950B2

Reaction notes

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