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 79233

반응식

HRID 79233 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-338a1a00fa8b451eb96d6336ac6249a7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841312B2

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