Sodium Bicarbonate → Tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176261ノート

反応式

HRID 1176261 の反応式
C([O:4][C:5]1[CH:6]=[C:7]([CH:43]=[CH:44][C:45]=1[Cl:46])[CH2:8][O:9][CH:10]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11]1)C=C.[BH4-].[Li+].C(=O)([O-])O.[Na+]>O1CCCC1.CC([O-])=O.CC([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd+2]>[Cl:46][C:45]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][CH:10]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])=[CH:18][CH:17]=3)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[CH2:11]2)=[CH:6][C:5]=1[OH:4]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68503445Tert-butyl 3-(3-allyloxy-4-chlorobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy)phenyl}piperidine-1-carboxylate

生成物 1

HCID 68506109Tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 84538Bis(triphenylphosphinepalladium) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

The solution of 1.53 g of tert-butyl 3-(3-allyloxy-4-chlorobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 15 ml of tetrahydrofuran is admixed with stirring successively with 0.018 g of bis(triphenylphosphine)palladium(II) acetate and 0.053 g of lithium borohydride. The reaction mixture is stirred at room temperature over 16 hours, subsequently poured onto saturated aqueous sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with water (100 ml) and brine (100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.45 (1:1 EtOAc-heptane); Rt=5.88.

後処理

  1. extractionextracted with tert-butyl methyl ether (2×100 ml)
  2. washThe organic phases are washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-fbdcb1788df7483b97565920d6aa35a0
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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