Sodium Bicarbonate → (2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine

HRID 481497

反応式

HRID 481497 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:21]([CH:23]([C:25]1[CH:26]=[CH:27][C:28]([O:33][CH3:34])=[C:29]([CH:32]=1)[CH:30]=O)[CH3:24])#[N:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][CH2:30][C:29]2[CH:32]=[C:25]([CH:23]([C:21]#[N:22])[CH3:24])[CH:26]=[CH:27][C:28]=2[O:33][CH3:34])[C@@H:3]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11311934(2S,3S)-3-Amino-1-tert-butoxycarbonyl-2-phenylpiperidineHCID 190664875-(1-Cyanoethyl)-2-methoxybenzaldehyde

生成物 1

HCID 57028229(2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine収率 103.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred and ice-cooled solution of Compound 17 (160 mg, 0.60 mmol) and Compound 14 (120 mg, 0.60 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (430 mg, 2.0 mmol) in one portion. The mixture was stirred at room temperature for 20 hours. The mixture was poured into NaHCO3 aq., and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give Compound 18 as a yellow oil (280 mg).

後処理

  1. stirringThe mixture was stirred at room temperature for 20 hours
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6d9f25a64db247fdb285099b400e9bed
出典データセット
uspto-grants-1998_08
特許番号
US05789423

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