Triethylamine → 1'-(1,1-Dimethylethyloxycarbonyl)-3-(methylsulfonyl)amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine)

HRID 1902166ノート

反応式

HRID 1902166 の反応式
[CH3:1][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([NH2:21])[CH2:13]2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:3][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:8][CH2:9][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([NH:21][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:13]2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18476131Tert-butyl 3-amino-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

生成物 1

HCID 233679991'-(1,1-Dimethylethyloxycarbonyl)-3-(methylsulfonyl)amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine)

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A sample of 1'-(1,1-Dimethylethyloxycarbonyl)-3-amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine), prepared by hydrogenation of 500 mg of oxime (1.58 mmole) as in Example 135 Step A, in 3.5 mL methylene chloride containing 475 mg of DMAP (2.46×1.58 mmole), and 550λ of triethylamine (2.51×1.58 mmole), was stirred under nitrogen in an ice bath while adding a solution of 270λ of methanesulfonyl chloride (2.2×1.58 mmole) in 3 mL methylene chloride dropwise over 2-3 minutes. The suspension was stored over night in the refrigerator. It was then washed twice with water, dried with magnesium sulfate and concentrated under reduced pressure to a gum. Preparative TLC on four 8"×8"×1,000 g GF silica gel plates using 1:2 ethyl acetate: hexane afforded the title compound, which crystallized on standing. Yield: 322 mg (54%)

後処理

  1. waitThe suspension was stored over night in the refrigerator
  2. washIt was then washed twice with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure to a gum

出典と根拠

ORDレコード
ord-393c9f8390c94906a37c4d7b3eb3dab2
出典データセット
uspto-grants-1996_11
特許番号
US05578593

反応ノート

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