9H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate → 9H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

HRID 876056ノート

反応式

HRID 876056 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][N:26](CC5C=CC=CC=5)[CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

3

反応物 1

HCID 582996729H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate

生成物 1

HCID 683226439H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate収率 61.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of compound 403 (1.43 g, 3.05 mmol) in ethanol (27 mL) was added palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol), followed by hydrochloric acid (0.10 mL). The sealed glass tube was then evacuated and purged with hydrogen three times. The sealed tube was then charged with hydrogen (50 psi), and allowed to stir at room temperature for three days. HPLC showed ˜85% conversion to the desired product. After filtering the mixture through a plug of celite, the filtrate was concentrated to a solid and purified by flash chromatography (0-20% methanol in DCM with 1% NH4OH) to give compound 404 (709 mg, 61%) as a white solid. LCMS-ESI (POS), M/Z, M+1: Found 379.1, Calculated 379.2.

後処理

  1. dry with materialpalladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol)
  2. customThe sealed glass tube was then evacuated
  3. custompurged with hydrogen three times
  4. additionThe sealed tube was then charged with hydrogen (50 psi)
  5. filtrationAfter filtering the mixture through a plug of celite
  6. concentrationthe filtrate was concentrated to a solid
  7. custompurified by flash chromatography (0-20% methanol in DCM with 1% NH4OH)

出典と根拠

ORDレコード
ord-75ef7ed4c1364084b509c29959fd8f00
出典データセット
uspto-grants-2015_03
特許番号
US08980903B2

反応ノート

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