Water → (1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

HRID 882794ノート

反応式

HRID 882794 の反応式
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[C@H:21]([CH:22]=O)[C@@H:20]2[CH2:24][C@H:17]1[CH2:18][CH2:19]2)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[C@H:21]([CH2:22][NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:20]2[CH2:24][C@H:17]1[CH2:18][CH2:19]2)=[O:15])([CH3:12])([CH3:10])[CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18396214(1R,3S,4S)-3-Formyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

生成物 1

HCID 66865917(1R,3S,4S)-3-(benzylamino-methyl)-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Benzylamine (49.7 mmol) is added to a solution of (1R,35,45)-3-formyl-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (49.7 mmol) in DCM (200 mL). The mixture is treated with sodium triacetoxyborohydride (69.6 mmol), stirred for additional 20 min, poured into water (200 mL) and stirred vigorously for 10 min. The layers are separated and the aq. layer is extracted twice with DCM (2×100 mL). The combined organic layers are washed with sat. NaHCO3 solution (100 mL), water (100 mL) and brine (150 mL), dried over MgSO4 and treated with activated charcoal (5 g). The mixture is filtered through celite and the filtrate is concentrated in vacuo to give the desired benzylamine which is used without further purification. LC-MS (basic): tR=1.00 min; [M+H]+=317.3.

後処理

  1. stirringstirred vigorously for 10 min
  2. customThe layers are separated
  3. extractionthe aq. layer is extracted twice with DCM (2×100 mL)
  4. washThe combined organic layers are washed with sat. NaHCO3 solution (100 mL), water (100 mL) and brine (150 mL)
  5. dry with materialdried over MgSO4
  6. additiontreated with activated charcoal (5 g)
  7. filtrationThe mixture is filtered through celite
  8. concentrationthe filtrate is concentrated in vacuo

出典と根拠

ORDレコード
ord-df7f30b9ce3144ecbc922a4df094a7c1
出典データセット
uspto-grants-2012_08
特許番号
US08236801B2

反応ノート

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