Acetic Acid → Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate

HRID 895466

反応式

HRID 895466 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClC(Cl)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 4316940Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate収率 87.4%

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of piperazine-1-carboxylic acid tert-butyl ester (4.00 g, 21.5 mmol) in dry dichloroethane (70 mL) are added 3-chlorobenzaldehyde (2.49 mL, 3.08 g, 21.9 mmol), HOAc (2.58 mL, 2.71 g, 45.1 mmol) and NaBH(OAc)3 (5.46 g, 25.8 mmol) at ambient temperature. After stirring at ambient temperature for 3d, 2N NaOH (40 mL) is added, the layers are separated, and the aqueous layer is extracted with CH2Cl2 (4×50 mL). The combined organic extracts are washed with water (3×50 mL) and brine (80 mL) and dried over MgSO4. The crude material is purified by chromatography on silica gel, eluting with hexane:EtOAc mixtures, yielding 5.83 g (18.8 mmol, 87%) of the title compound as yellow oil. MS (ES): m/z 311.0/313.0 (50/18) [MH+]. tR (method A)=5.0 min.

後処理

  1. additionis added
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with CH2Cl2 (4×50 mL)
  4. washThe combined organic extracts are washed with water (3×50 mL) and brine (80 mL)
  5. dry with materialdried over MgSO4
  6. customThe crude material is purified by chromatography on silica gel
  7. washeluting with hexane

出典と根拠

ORDレコード
ord-1de5866408e84ce6b7262895363e3a82
出典データセット
uspto-grants-2005_07
特許番号
US06916804B2

関連ノート

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