Phosphoric Acid → HCID 22335637, compound

HRID 586641Notes

Reaction equation

HRID 586641 reaction equation
[CH3:1][CH:2]([CH3:20])[C:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]2[N:11]([C:12]=1[CH3:13])[CH2:10][CH2:9][CH2:8]2)=O.[BH3-]C#N.[Na+].OP(O)(O)=O>C(Cl)Cl.[Zn+2].[I-].[I-]>[CH2:3]([C:5]1[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]2[N:11]([CH2:10][CH2:9][CH2:8]2)[C:12]=1[CH3:13])[CH:2]([CH3:20])[CH3:1]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 5003444Sodium cyanoborohydrideHCID 22335604HCID 22335604, compound

Product 1

HCID 22335637HCID 22335637, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-1-(3-methyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)-propan-1-one (7.5 g, 28 mmol) in CH2Cl2 (140 ml) is treated successively with NaCNBH3 (7.4 g, 112 mmol) and ZnI2 (12.5 g, 40 mmol) and the mixture is stirred at RT for 2 h (TLC: SiO2/diethyl ether; starting material Rf 0.75; product Rf 8.8). The mixture is covered with a layer of H3PO4 (8%, 200 ml) with ice cooling and stirred for 16 h. The CH2Cl2 phase is separated and washed with water (50 ml), dried over Na2SO4 sicc. and concentrated in vacuo. The residue (7.5 g, 106%) is recrystallized from MeOH.

Workup

  1. customThe CH2Cl2 phase is separated
  2. washwashed with water (50 ml)
  3. dry with materialdried over Na2SO4 sicc
  4. concentrationand concentrated in vacuo
  5. customThe residue (7.5 g, 106%) is recrystallized from MeOH

Sources & evidence

ORD record
ord-cd766c6b00c3478cb9eb32091fa47423
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Reaction notes

Loading…