Benzyl Alcohol → tert-Butyl [{1-(2-benzyloxycarbonyl-2-methylpropyl)piperidin-4-yl}methyl]carbamate

HRID 16602

反応式

HRID 16602 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.Cl[CH2:17][C:18]([CH3:30])([CH3:29])[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].ClCC(C)(C)C(Cl)=O.C(O)C1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[I-].[Na+]>CN(C)C=O>[CH2:22]([O:21][C:19]([C:18]([CH3:30])([CH3:29])[CH2:17][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

8

反応物 6

HCID 244Benzyl AlcoholHCID 5238Sodium IodideHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 54294282Benzyl 3-chloropivalate

生成物 1

HCID 86602121tert-Butyl [{1-(2-benzyloxycarbonyl-2-methylpropyl)piperidin-4-yl}methyl]carbamate収率 1.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a stirred solution of tert-butyl (piperidin-4-ylmethyl)carbamate (38.8 g, 181 mmol) in N,N-dimethylformamide (100 mL) was added benzyl 3-chloropivalate {14.2 g, 124 mmol, prepared from 3-chloropivaloyl chloride (25.6 g, 165 mmol) and benzyl alcohol (19.6 g, 181 mmol), ethyldiisopropylamine (64.0 g, 495 mmol) and sodium iodide (27.1 g, 181 mmol) at ambient temperature. The resulting mixture was stirred at 120° C. for 14 h. The volatile components were removed by evaporation and the resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (1:1) to give 640 mg (1%) of the title compound as a pale yellow oil.

後処理

  1. customThe volatile components were removed by evaporation
  2. customthe resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-51017605c27a4df0905c4c42548db89d
出典データセット
uspto-grants-2010_06
特許番号
US07737163B2

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