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Diisopropylethylamine → 1-(s)-(1-(r)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-2-(r)-(4-fluorophenyl)-3-(r)-(((2-benzyloxycarbonylethyl)methylamino)-methyl)cyclopentane

HRID 1017766
ノート
印刷プレビュー

反応式

HRID 1017766 の反応式
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18](C=O)[C@@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl.[CH2:33]([O:40][C:41](=[O:46])[CH2:42][CH2:43][NH:44][CH3:45])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:47]CN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([CH2:45][N:44]([CH2:43][CH2:42][C:41]([O:40][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:46])[CH3:47])[C@@H:17]2[C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 228974301-(S)-(1-(R)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-2-(R)-(4-fluorophenyl)-3-(R)-(formyl)cyclopentaneHCID 69355610Benzyl 3-(methylamino)propanoate hydrochloride

生成物 1

HCID 22897425
1-(s)-(1-(r)-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-2-(r)-(4-fluorophenyl)-3-(r)-(((2-benzyloxycarbonylethyl)methylamino)-methyl)cyclopentane

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of 500 mg of aldehyde from Step A in 5 mL of 1,2-dichloroethane was added 320 mg of N-methyl-β-alanine benzyl ester hydrochloride and 0.24 mL of DIPEA. After stirring at room temperature for 10 minutes, 470 mg of sodium triacetoxyborohydride was added. The reaction was stirred for 16 hr. The reaction was quenched with sat'd sodium bicarbonate and was extracted twice with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, combined and evaporated. The residue was purified by FC (20-30% ethyl acetate/hexanes) to give 564 mg of title compound.

後処理

  1. stirringThe reaction was stirred for 16 hr
  2. customThe reaction was quenched with sat'd sodium bicarbonate
  3. extractionwas extracted twice with methylene chloride
  4. washThe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by FC (20-30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-34798065ea354a72a035eb287aa21636
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06479518B2

反応ノート

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