3-Methylbutanal → 2-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1436505ノート

反応式

HRID 1436505 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:38][CH:39]([CH3:43])[CH2:40][CH:41]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:41][CH2:40][CH:39]([CH3:43])[CH3:38])[CH2:10][C@@H:9]1[C@@H:14]([OH:37])[C@H:15]([N:23]=[C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 115523-MethylbutanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866153742-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866153762-(R)-[2-(R)-(Benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-4-(3-methyl-butyl)-piperazine-1-carboxylic acid tert-butyl ester収率 87.8%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Dissolve (2-(R)-[2-(R)-(benzhydrylidene-amino)-1-(S)-hydroxy-3-phenylpropyl]-piperazine-1-carboxylic acid tert-butyl ester (167 mg, 0.33 mmol) in 1,2-dichloroethane (2.5 mL) and add 3-methylbutyraldehyde (0.042 mL, 0.41 mmol). After 5 min, add sodium triacetoxyborohydride (100 mg, 0.47 mmol) and stir for 1 h. Add saturated aqueous sodium bicarbonate solution (5 mL) and stir for 10 min. Add ethyl acetate and separate the layers. Extract the aqueous layer with ethyl acetate, combine the organic layers, wash the organic layer with saturated aqueous sodium chloridesolution, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with ethyl acetate) to give the title compound as a colorless oil (165 mg, 87%).

後処理

  1. customAdd ethyl acetate and separate the layers
  2. extractionExtract the aqueous layer with ethyl acetate
  3. washwash the organic layer with saturated aqueous sodium chloridesolution
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with ethyl acetate)

出典と根拠

ORDレコード
ord-7b15a8e5e4374255aaf5b70ac1f64636
出典データセット
uspto-grants-2009_11
特許番号
US07618978B2

反応ノート

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