Sodium Bicarbonate → HCID 68501582, compound

HRID 1176213Notes

Reaction equation

HRID 1176213 reaction equation
C([O:4][C:5]1[CH:45]=[CH:44][C:8]([CH2:9][O:10][CH:11]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:19][CH:18]=3)[CH2:15][CH2:14][N:13]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:12]2)=[CH:7][C:6]=1[N+:46]([O-])=O)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]>[NH2:46][C:6]1[CH:7]=[C:8]([CH:44]=[CH:45][C:5]=1[OH:4])[CH2:9][O:10][CH:11]1[CH:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[CH:19][CH:18]=2)[CH2:15][CH2:14][N:13]([C:37]([O:39][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:38])[CH2:12]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68502841HCID 68502841, compound

Product 1

HCID 68501582HCID 68501582, compound

Reagents, catalysts & solvents 2

HCID 84538Palladium(2+) acetate--triphenylphosphane (1/2/2)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

The solution of 2.16 g of tert-butyl 3-(4-allyloxy-3-nitrobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 15 ml of tetrahydrofuran is admixed with stirring at room temperature with 0.025 g of bis(triphenylphosphine)palladium(II) acetate and 0.075 g of lithium borohydride and stirred at room temperature for 2.5 hours. The reaction mixture is poured onto 1M sodium hydrogencarbonate (50 ml) and extracted with tert-butyl methyl ether (2×50 ml). The organic phases are washed with water (50 ml) and brine (50 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=0.38 (1:1 EtOAc-heptane); Rt=6.02.

Workup

  1. extractionextracted with tert-butyl methyl ether (2×50 ml)
  2. washThe organic phases are washed with water (50 ml) and brine (50 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-316a1fc9fe8942d982c3911f2c31608d
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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