Trifluoroacetic acid → (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholine

HRID 369800Notes

Reaction equation

HRID 369800 reaction equation
[O:1]=[C:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]3[CH2:18][CH2:17][CH2:16]3)[CH:10]=2)[N:6](C(OC(C)(C)C)=O)[C@@H:5]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:4]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:3]1.C(O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[O:1]=[C:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]3[CH2:18][CH2:17][CH2:16]3)[CH:10]=2)[NH:6][C@@H:5]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:4]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:3]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 57135938tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)-4-morpholinecaboxylate

Product 1

HCID 57005921(2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to example 82, 1.87 g of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)-4-morpholinecarboxylate was treated with 3.1 mL of TFA in 30 mL of CH2Cl2 for 4 h. Neutralization with 8 mL of Et3N and work-up in the usual manner gave a light yellow residue. Purification of the crude material by flash chromatography on 85 g of silica gel (8:2 hexane:EtOAc) afforded 1.35 g (91%) of (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholine as a thick, transparent semi-solid.

Workup

  1. customgave a light yellow residue
  2. customPurification of the crude material by flash chromatography on 85 g of silica gel (8:2 hexane:EtOAc)

Sources & evidence

ORD record
ord-5516c9b706d74e6ea8456bd76264c038
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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