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

HRID 1182243노트

반응식

HRID 1182243 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)촉매HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-e43d1ca801f642b7a7c048b3c4efd6f7
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288563B2

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