Ammonium Chloride → HCID 178486034、化合物

HRID 25643ノート

反応式

HRID 25643 の反応式
[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH:15]=[C:16](Br)Br)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.CN1C(=O)N(C)CCC1.Br[CH2:35][CH2:36][O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1.[NH4+].[Cl-]>C1COCC1>[C:1]([O:5][C:6](=[O:19])[N:7]([CH3:8])[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:35][CH2:36][O:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 5

HCID 25517Ammonium ChlorideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 178418339ButyllithiumHCID 178486027HCID 178486027、化合物

生成物 1

HCID 178486034HCID 178486034、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 10.0 g (25.2 mmol) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 400 ml THF was treated at −78° C. with 33.0 ml (68.3 mmol) of BuLi (ca 1.6 M in hexane) and stirred for 2 h, then 27.8 ml (230.4 mmol) of DMPU were added and 10 min later 19.0 ml (125.9 mmol) of 2-(2-bromoethoxy)tetrahydro-2H-pyran dissolved in 20 ml were dropped in during 20 min. The reaction was warmed up to RT and stirred over night (approx. 16 h). An aqueous solution of saturated NH4Cl was added and the mixture was extracted with ether (3×). The organic phase was washed with H2O (2×), aqueous 10% NaCl and dried with Na2SO4, filtered and evaporated to give after flash column chromatography on silica gel (Hexane/EtOAc 19:1 to 3:1) 3.5 g (38%) of trans-Methyl-{4-[4-(tetrahydro-pyran-2-yloxy)-but-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester, MS: 366 (MH+).

後処理

  1. dissolutiondissolved in 20 ml
  2. additionwere dropped in during 20 min
  3. stirringstirred over night (approx. 16 h)
  4. extractionthe mixture was extracted with ether (3×)
  5. washThe organic phase was washed with H2O (2×), aqueous 10% NaCl
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-3434bbfe2c2a499c9641e5a0424417c2
出典データセット
uspto-grants-2005_02
特許番号
US06858651B2

反応ノート

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