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

HRID 409586ノート

反応式

HRID 409586 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-ccae2a5dd49a45eda9bff0849fba2861
出典データセット
uspto-grants-2014_06
特許番号
US08759387B2

反応ノート

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