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1,2-Dichloroethane → 8-(1-Benzyl-4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2-(4-bromobenzyl)-2,8-diaza-spiro[4.5]decan-1-one dihydrochloride

HRID 1182163
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HRID 1182163 반응식
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][C:9]3([CH2:16][CH2:15][N:14]([CH2:17][CH:18]4[CH:22]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:21][NH:20][CH2:19]4)[CH2:13][CH2:12]3)[C:8]2=[O:29])=[CH:4][CH:3]=1.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Cl:53]CCCl>>[ClH:53].[ClH:53].[CH2:32]([N:20]1[CH2:21][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]([CH2:17][N:14]2[CH2:13][CH2:12][C:9]3([C:8](=[O:29])[N:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:31][CH:30]=4)[CH2:11][CH2:10]3)[CH2:16][CH2:15]2)[CH2:19]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 111,2-DichloroethaneHCID 240BenzaldehydeHCID 2724942TriacetoxyborohydrideHCID 673687102-(4-Bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

생성물 1

HCID 673706578-(1-Benzyl-4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2-(4-bromobenzyl)-2,8-diaza-spiro[4.5]decan-1-one dihydrochloride수율 39.5%

실험 절차

A solution of 28.9 mg (60 μmol) of 2-(4-bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one and 6.3 mg (60 μmol) of benzaldehyde in 1.5 mL of DCE was agitated for 10 minutes at room temperature before adding 20 mg (90 μmol) of triacetoxyborohydride. The reaction mixture was then stirred overnight and quenched with a saturated solution of sodium bicarbonate (1 mL). The solution was extracted with DCM (2×2 mL) and the combined organic layers were concentrated. The crude was purified by semi-preparative HPLC (method B) yielding 15.3 mg (39.5%) of Compound 98 as a pale yellow solid.

후처리

  1. customquenched with a saturated solution of sodium bicarbonate (1 mL)
  2. extractionThe solution was extracted with DCM (2×2 mL)
  3. concentrationthe combined organic layers were concentrated
  4. customThe crude was purified by semi-preparative HPLC (method B)

출처 및 근거

ORD 기록
ord-ed32c18d5b334a5db57a0406aea0b13e
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07288548B2

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