Methyl morpholine oxide → 5-oxo-6-propyl-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester

HRID 1182243Notes

Reaction equation

HRID 1182243 reaction equation
[C:1]([O:5][C:6](=[O:17])[N:7]([CH2:14][CH:15]=[CH2:16])[CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:22][CH2:21]C1>ClCCl.[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[C:1]([O:5][C:6]([N:7]1[CH2:14][CH:15]2[CH2:16][C:21](=[O:22])[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]2[CH2:8]1)=[O:17])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86600396Allyl-hex-2-ynyl-carbamic acid tert-butyl ester

Product 1

HCID 692253565-oxo-6-propyl-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl esterYield 38.7%

Reagents, catalysts & solvents 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)CatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of allyl-hex-2-ynyl-carbamic acid tert-butyl ester (741 mg) in dichloromethane (50 mL) was added to dicobalt octacarbonyl (1.12 g) under an argon atmosphere. The resulting solution was stirred at room temperature for 1.5 h. After this time, N-methylmorpholine N-oxide (2.56 g) was added in portions during a 60 min period. Upon completion of addition, the reaction mixture was stirred for an additional 2.5 h. At the conclusion of this period, the mixture was filtered through silica gel, and the solid was washed with a 1:1 ethyl acetate-hexane solution (200 mL). The filtrate was concentrated under vacuum to yield a residue. The residue was purified by flash column chromatography to provide the title compound as a light brown oil (321 mg). MS (ES+) m/z 266.19 (M+H+).

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred for an additional 2.5 h
  3. filtrationAt the conclusion of this period, the mixture was filtered through silica gel
  4. washthe solid was washed with a 1:1 ethyl acetate-hexane solution (200 mL)
  5. concentrationThe filtrate was concentrated under vacuum
  6. customto yield a residue
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-e43d1ca801f642b7a7c048b3c4efd6f7
Source dataset
uspto-grants-2007_10
Patent number
US07288563B2

Reaction notes

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