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Water → trans-Tert-butyl 8-fluoro-5-methyl-6-oxo-1,3a,4,5,6,10b-hexahydrobenzo[c]pyrrolo[3,4-e]azepine-2(3h)-carboxylate

HRID 84956
Notes
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Reaction equation

HRID 84956 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@@H:11]3[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C@H:10]3[CH2:9][NH:8][C:7](=[O:22])[C:6]=2[CH:23]=1.I[CH3:25].[H-].[Na+].O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@@H:11]3[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:14][C@H:10]3[CH2:9][N:8]([CH3:25])[C:7](=[O:22])[C:6]=2[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67166997HCID 67166997, compound

Product 1

HCID 67168442trans-Tert-butyl 8-fluoro-5-methyl-6-oxo-1,3a,4,5,6,10b-hexahydrobenzo[c]pyrrolo[3,4-e]azepine-2(3h)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of Example 224A (3.8 g, 11.9 mmol) and iodomethane (2.1 g, 15 mmol) in tetrahydrofuran (15 mL) was added NaH (0.6 g, 60%, 15 mmol) in portions at 0° C. The mixture was stirred for 2 hours and water was then added. The precipitates were collected to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.33 (m, 1H), 7.29 (m, 1H), 7.28 (m, 1H), 3.69 (m, 1H), 3.60 (m, 1H), 3.54 (m, 1H), 3.35 (m, 2H), 3.17 (m, 1H), 3.10 (s, 3H), 3.00 (m, 1H), 2.16 (m, 1H), and 1.43 (s, 9H).

Workup

  1. customThe precipitates were collected

Sources & evidence

ORD record
ord-34c8b43decd847ecbca4807eaa39b063
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846951B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes