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Potassium Carbonate → (8S,9aS)-8-hydroxy-2-[5-(trifluoromethyl)pyridin-2-yl]octahydro-5H-pyrrolo[1,2-a][1,4]diazepin-5-one

HRID 572035
Notes
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Reaction equation

HRID 572035 reaction equation
[O:1]=[C:2]1[N:8]2[CH2:9][C@H:10](C3C=C([N+]([O-])=O)C=CC=3C([O-])=O)[CH2:11][C@H:7]2[CH2:6][N:5]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-:35].[K+].[K+].C(OCC)(=O)C.CO>CO>[OH:35][C@@H:10]1[CH2:9][N:8]2[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][N:25]=3)[CH2:6][C@@H:7]2[CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21584119Ethylacetate methanolHCID 86723185(8S,9aS)-5-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]octahydro-1H-pyrrolo[1,2-a][1,4]diazepin-8-yl-4-nitrobenzoate

Product 1

HCID 86723184(8S,9aS)-8-hydroxy-2-[5-(trifluoromethyl)pyridin-2-yl]octahydro-5H-pyrrolo[1,2-a][1,4]diazepin-5-oneYield 142.2%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To (8S,9aS)-5-oxo-2-[5-(trifluoromethyl)pyridin-2-yl]octahydro-1H-pyrrolo[1,2-a][1,4]diazepin-8-yl-4-nitrobenzoate (135 mg, 0.291 mmol, Part C) in methanol (2.5 mL) was added potassium carbonate (24 mg, 0.174 mmol). The mixture was stirred at room temperature for 1.5 hours and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate, then ethyl acetate/methanol=10:1) to give 78 mg (85% yield) of the titled compound as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.72 (m, 1H), 2.28 (m, 1 H), 2.45 (m, 1H), 2.63 (m, 1 H), 3.35 (m, 3 H), 3.44 (m, 1 H), 3.92 (m, 1H), 4.17 (m, 1H), 4.42 (m, 2H), 5.09 (br s, 1H), 7.00 (d, J=8 Hz, 1 H), 7.80 (d, J=8 Hz, 1 H), 8.43 (s, 1 H); MS (ESI) m/z 316.0 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-41ce7c43b334482f9cb6c1e387c0b2c4
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029361B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes