Trifluoroacetic acid → (6aR,7S,9aS,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417627Notes

Reaction equation

HRID 1417627 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:42])[C@@H:30]([CH3:41])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:40])([CH3:39])[C:35](=O)[CH2:36][CH2:37][C@@:27]34[O:26][C:11]=2[C:12]2[CH2:13][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:43][N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.FC(F)(F)C(O)=O>C(O)C>[CH2:1]([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:42])[C@@H:30]([CH3:41])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:39])([CH3:40])[C:35](=[N:43][N:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)[CH2:36][CH2:37][C@@:27]34[O:26][C:11]=2[C:12]2[CH2:13][N:14]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C:15](=[O:18])[C:16]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 20315N-AminomorpholineHCID 86753805(6aR,7S,9aS,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3, 11-dioxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753835(6aR,7S,9aS,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound (37) (573 mg, 1.00 mmol) in 60 ml of ethanol were added 306 mg (3.00 mmol) of N-aminomorpholine and 328 μl (3.51 mmol) of trifluoroacetic acid. The reaction was allowed to proceed for 72 hours. The reaction mixture was then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 100 g; n-hexane:ethyl acetate=7:3) to give 265 mg (40%) of Compound (60).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by a silica gel column chromatography (silica gel 100 g; n-hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-fe0a3d338f6c45bfaf3e5b2f66b74412
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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