Benzylamine → HCID 10852331、化合物

HRID 1257670ノート

反応式

HRID 1257670 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([F:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]([F:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]([F:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

生成物 2

HCID 10852331HCID 10852331、化合物収率 26%HCID 11312869cis-4-Benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine収率 23%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A stirred solution of 3-Fluoro-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (2.00 g, 9.21 mmol) in methanol (20 ml) and acetic acid (1 ml) was treated with benzyl amine (1.106 ml, 10.013 mmol) and stirred at ambient temperature for three hours. The mixture was then treated with sodium cyanoborohydride (0.8678 g, 13.81 mmol) and left to stand overnight. The reaction was quenched with a saturated solution of sodium bicarbonate (20 ml) and extracted with three portions of dichloromethane (50 ml). Combined organic layers were dried with magnesium sulfate and concentrated under vacuum to give crude product. Purification by column chromatography on silica gel (gradient: 0 to 60% ethyl acetate in heptane) gave 734 mg (26%) of trans-4-benzylamino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester and 653 mg (23%) of cis-4-benzylamino-3-fluoro-piperidine-1-carboxylic acid tert-butyl ester.

後処理

  1. waitleft
  2. waitto stand overnight
  3. customThe reaction was quenched with a saturated solution of sodium bicarbonate (20 ml)
  4. extractionextracted with three portions of dichloromethane (50 ml)
  5. dry with materialCombined organic layers were dried with magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customto give crude product
  8. customPurification by column chromatography on silica gel (gradient: 0 to 60% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-d38fef48098f449fb20c32a5a993613c
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

読み込み中…