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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
ノート
印刷プレビュー

反応式

HRID 1182163 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ed32c18d5b334a5db57a0406aea0b13e
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07288548B2

反応ノート

読み込み中…

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