Chloroform → N-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

HRID 1811632ノート

反応式

HRID 1811632 の反応式
C[O:2][C:3]([C@@H:5]([NH:7][C:8](=[O:33])[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C@@H:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:16]2)=[CH:11][CH:10]=1)[CH3:6])=O.[BH4-].[Li+].[Cl-].[NH4+].C(Cl)(Cl)Cl>C1COCC1>[OH:2][CH2:3][C@@H:5]([NH:7][C:8](=[O:33])[C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C@@H:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH3:22])[CH2:16]2)=[CH:13][CH:14]=1)[CH3:6]

参加物

6

反応物 4

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 58973534N-[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

生成物 1

HCID 58973487N-[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide収率 49.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In 1 ml of THF was dissolved 31.9 mg of N—[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide, 3.0 mg of lithium borohydride was added thereto, and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and chloroform was added to the mixture and the mixture was stirred and then the liquids were separated. The organic layer was dried and evaporated, and then, the residue was purified by NH silica gel thin-layer chromatography (chloroform:methanol=95:5) to obtain 14.7 mg of N—[(S)-1-hydroxypropan-2-yl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide (the following Table X, Example 12.003).

後処理

  1. additionwas added
  2. additionwas added to the mixture
  3. stirringthe mixture was stirred
  4. customthe liquids were separated
  5. customThe organic layer was dried
  6. customevaporated
  7. customthe residue was purified by NH silica gel thin-layer chromatography (chloroform:methanol=95:5)

出典と根拠

ORDレコード
ord-a8c7fd485b104b4b98a82d56e04d45f6
出典データセット
uspto-grants-2013_01
特許番号
US08362274B2

反応ノート

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