Formaldehyde → HCID 178484111、化合物

HRID 1169411ノート

反応式

HRID 1169411 の反応式
Cl.[NH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5]1.[O:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCCl.O.C(N(CC)CC)C>[CH3:28][N:2]([CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:6][CH2:5]1)[CH:24]1[CH2:25][CH2:26][O:21][CH2:22][CH2:23]1

参加物

8

反応物 4

HCID 712FormaldehydeHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydride2 回HCID 178479229HCID 178479229、化合物

生成物 1

HCID 178484111HCID 178484111、化合物収率 61%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of benzyl trans-4-aminomethylcyclohexylcarbamate hydrochloride (11.56 g), tetrahydro-4H-pyran-4-one (3.85 g), triethylamine (8 ml) and 1,8-diazabicyco[5,4,0]-7-undecene (5.85 g) in 1,2-dichloroethane (100 ml) was added at room temperature sodium triacetoxyborohydride (8.96 g), and the resulting mixture was stirred for 14 hours. To the reaction mixture were added 37% formalin (3.43 g) and sodium triacetoxyborohydride, and the resulting mixture was stirred further for 7 hours. The reaction mixture was mixed with water and was extracted with dichloromethane. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. After the resulting organic layer was concentrated under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethanol/ethyl acetate 1:4→1:2) to obtain benzyl trans-4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]cyclohexylcarbamate (8.45 g) as colorless crystals.

後処理

  1. stirringthe resulting mixture was stirred further for 7 hours
  2. extractionwas extracted with dichloromethane
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. concentrationAfter the resulting organic layer was concentrated under reduced pressure
  6. customthe residue was subjected to separation and purification

出典と根拠

ORDレコード
ord-bedf14313aed44b087640adbbeff5545
出典データセット
uspto-grants-2003_09
特許番号
US06627651B1

反応ノート

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