Sodium triacetoxyborohydride → HCID 68828337、化合物

HRID 2099351ノート

反応式

HRID 2099351 の反応式
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@H:7]([C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:15]3)=[O:10])[NH2:8])=[CH:4][CH:3]=1.[C:35]([N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]1=O)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([NH:8][CH:45]2[CH2:46][CH2:47][N:42]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:43][CH2:44]2)[C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:15]3)=[O:10])=[CH:33][CH:34]=1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 68829063HCID 68829063、化合物

生成物 1

HCID 68828337HCID 68828337、化合物収率 65.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.41 g of N-[8-(4-chloro-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea is dissolved in 4 ml of dichloromethane under N2 in the presence of 0.17 g of N-BOC-piperidone and of 0.23 g of sodium triacetoxyborohydride, and the mixture is stirred at ambient temperature for 16 h. After evaporation and hydrolysis, extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. Drying over MgSO4 and concentration to dryness are carried out. The crude is chromatographed on silica gel, elution being carried out with a 98/2 mixture of dichloromethane and methanol. 0.37 g of tert-butyl 4-{[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo-[3.2.1]oct-8-yl)-2-oxoethyl]amino}piperidine-1-carboxylate is then obtained.

後処理

  1. customAfter evaporation and hydrolysis, extraction
  2. washThe organic phase is washed with H2O
  3. dry with materialDrying over MgSO4 and concentration to dryness
  4. customThe crude is chromatographed on silica gel, elution
  5. additionbeing carried out with a 98/2 mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-0b5e6f590b2b48d39c628b6a42fe775f
出典データセット
uspto-grants-2009_08
特許番号
US07569582B2

反応ノート

読み込み中…