Ammonium Chloride → HCID 178486034, compound

HRID 1743774Notes

Reaction equation

HRID 1743774 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

HCID 178486034HCID 178486034, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 Et2O (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+).

Workup

  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 Et2O (3×)
  5. washThe organic phase was washed with H2O (2×), aqueous 10% NaCl
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5a586c992e2e4c4d9426ebf5c5f1fda3
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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