Ammonia → Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamate

HRID 227933ノート

反応式

HRID 227933 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([OH:22])=O)([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:24]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.N>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][CH2:18][C:15]([C:20]([NH2:24])=[O:22])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 106622014-(Benzyloxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid

生成物 1

HCID 23150697Benzyl (4-carbamoylbicyclo[2.2.2]octan-1-yl)carbamate収率 89.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxylic acid (998 mg) was suspended in acetonitrile (20 mL). While the suspension was chilled in an ice bath, N-hydroxybenzotriazole (605 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (757 mg) were sequentially added. The mixture was stirred at room temperature for 4 hours and was left overnight. Subsequently, 25% aqueous ammonia (1.80 mL) was added while the reaction vessel was chilled in an ice bath. The mixture was then stirred at room temperature for 1 hour. The insoluble material was filtered and washed sequentially with acetonitrile and dichloromethane. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:ethyl acetate) to give 4-benzyloxycarbonylaminobicyclo[2.2.2]octane-1-carboxamide (889 mg).

後処理

  1. temperatureWhile the suspension was chilled in an ice bath
  2. waitwas left overnight
  3. temperaturewas chilled in an ice bath
  4. stirringThe mixture was then stirred at room temperature for 1 hour
  5. filtrationThe insoluble material was filtered
  6. washwashed sequentially with acetonitrile and dichloromethane
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (eluant:ethyl acetate)

出典と根拠

ORDレコード
ord-ec25fb55fb3b45baa7db8d7d33612a69
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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