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Water → tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylate

HRID 1022677
ノート
印刷プレビュー

反応式

HRID 1022677 の反応式
C[Li].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10].I[CH2:27]I.O>C(OCC)C.C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][C:12]32[O:25][CH2:27]3)[CH:7]=[CH:8][C:9]=1[Cl:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 6346DiiodomethaneHCID 66976649HCID 66976649、化合物HCID 178418348HCID 178418348、化合物

生成物 1

HCID 86663865tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylate収率 18.9%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution (3 M, 0.56 mL) of methyllithium in diethyl ether was added to a solution of tert-butyl (7RS)-7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate (300 mg) and diiodomethane (335 mg) in THF (3 mL), and the mixture was stirred at 0° C. for 30 min, and at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and HPLC to give the title compound (59 mg).

後処理

  1. waitat room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography and HPLC

出典と根拠

ORDレコード
ord-ee75f13362074becadb02eff9adece36
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722662B2

反応ノート

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