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Acetic Acid → 5-(trifluoromethyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

HRID 12758
ノート
印刷プレビュー

反応式

HRID 12758 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[C:4](=[O:15])[NH:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH:12]=O)[CH:8]=1.[F:18][C:19]([F:33])([F:32])[C:20]1[CH:25]=[CH:24][C:23]([C@:26]23[CH2:31][C@H:30]2[CH2:29][NH:28][CH2:27]3)=[CH:22][CH:21]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:52]C(Cl)C>C(OCC)(=O)C>[ClH:52].[F:1][C:2]([F:17])([F:16])[C:3]1[C:4](=[O:15])[NH:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:28]2[CH2:29][C@H:30]3[C@:26]([C:23]4[CH:22]=[CH:21][C:20]([C:19]([F:18])([F:33])[F:32])=[CH:25][CH:24]=4)([CH2:31]3)[CH2:27]2)[CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 589941974-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyraldehydeHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 86615952
5-(trifluoromethyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride
収率 76%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-(5-trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyraldehyde (Prep24, 22 mg, 0.09 mmol) in dichloroethane (1 mL), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 204 mg, 0.09 mmol), AcOH (7.9 mg, 0.13 mmol) and NaBH(AcO)3 (22 mg, 0.18) were added and the mixture was stirred at room temperature overnight. Ethyl acetate was added and the solution was washed with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-1) to give the title compound (31 mg, 76% yield) as a free base.

後処理

  1. washthe solution was washed with aqueous saturated NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (95-5-1)

出典と根拠

ORDレコード
ord-21ed03dc71274ef3b0a08a758c9b90cc
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07727988B2

反応ノート

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