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

HRID 130376ノート

反応式

HRID 130376 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 692253565-oxo-6-propyl-3,3a,4,5-tetrahydro-1H-cyclopenta[c]pyrrole-2-carboxylic acid tert-butyl ester収率 38.8%

試薬・触媒・溶媒 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of allyl-hex-2-ynyl-carbamic acid tert-butyl ester (741 mg, 3.12 mmol) in dichloromethane (50 mL) was added to dicobalt octacarbonyl (1.12 g, 3.28 mmol) 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, 21.9 mmol) 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 a light brown oil (321 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 5.3-3.9 (m, 3H), 3.17 (m, 1H), 2.80 (m, 1H), 2.67 (m, 1H), 2.29 (m, 1H), 2.13 (m, 2H), 1.51 (m+2s, 11H), 0.91 (m, 3H). MS (ES+) m/z 266.19 (M+H+).

後処理

  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

出典と根拠

ORDレコード
ord-f4442d268346425d8e14694855f5fdc7
出典データセット
uspto-grants-2008_06
特許番号
US07381738B2

反応ノート

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