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Acetic Acid → (1R,2S,3R)-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}cyclopentane-1,2-diol

HRID 1401857
ノート
印刷プレビュー

反応式

HRID 1401857 の反応式
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@@H:5]([OH:8])[C@H:4]1[OH:9].CCN(C(C)C)C(C)C.[CH3:19][C:20]1([CH3:44])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([C:32]3[N:33]=[C:34]([N:37]4[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]4)[S:35][CH:36]=3)[CH:23]=[CH:22][C:21]1=2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1.CN(C=O)C>[CH3:19][C:20]1([CH3:44])[CH2:29][CH2:28][C:27]([CH3:30])([CH3:31])[C:26]2[CH:25]=[C:24]([C:32]3[N:33]=[C:34]([N:37]4[CH2:42][CH2:41][CH:40]([NH:2][C@@H:3]5[CH2:7][CH2:6][C@@H:5]([OH:8])[C@H:4]5[OH:9])[CH2:39][CH2:38]4)[S:35][CH:36]=3)[CH:23]=[CH:22][C:21]1=2
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13497975(1R,2S,3R)-3-aminocyclopentane-1,2-diol hydrochlorideHCID 673225751-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one

生成物 1

HCID 67325209(1R,2S,3R)-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}cyclopentane-1,2-diol

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

24 mg (0.16 mmol) of (1R,2S,3R)-3-aminocyclopentane-1,2-diol hydrochloride are dissolved in 1 ml of THF and 2 ml of DMF, and 27 μl (0.16 mmol) of DIPEA are added. 60 mg (0.16 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one are added. The mixture is stirred at room temperature for 30 min, 18 μl (0.32 mmol) of glacial acetic acid are added, and the mixture is stirred for a further 10 min. 70 mg (0.32 mmol) of sodium triacetoxyborohydride are subsequently added. The reaction mixture is stirred at room temperature overnight, a concentrated sodium hydrogencarbonate solution is added, and the mixture is extracted twice with EA. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is purified by means of preparative HPLC. The product is in the form of the hydrochloride.

後処理

  1. stirringthe mixture is stirred for a further 10 min
  2. stirringThe reaction mixture is stirred at room temperature overnight
  3. extractionthe mixture is extracted twice with EA
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-61cc98d5346442cd9b79d5e2369b4404
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08907098B2

反応ノート

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