Sulfuric Acid → HCID 22406704, compound

HRID 440518Notes

Reaction equation

HRID 440518 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]=[C:16]2[C:19]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH2:21][CH2:20]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)COC(N1CCC[C@H]1C(O[BH-](OC(=O)[C@@H]1CCCN1C(OCC(C)C)=O)OC(=O)[C@@H]1CCCN1C(OCC(C)C)=O)=O)=O.[Na+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH:16]2[C:19]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[CH2:20][CH2:21]2)=[CH:11][C:10]=1[O:29][CH3:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 22406910HCID 22406910, compoundHCID 131719405HCID 131719405, compound

Product 1

HCID 22406704HCID 22406704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-benzyloxy-1-[1-(2-chlorophenyl)cyclopropyl]-6-methoxy-3,4-dihydroisoquinoline (0.5 g, prepared in a similar manner to that described in Example CA281) in dichloromethane (10 ml) was added dropwise at -40° C. to a stirred solution of sodium tris[N-(2-methylpropyloxycarbonyl)prolyloxy]borohydride (2.43 g) in dichloromethane (10 ml). The mixture was allowed to reach ambient temperature and was stirred for 49 hours. Dilute sulphuric acid (10 ml, 10% v/v) was added, and stirring continued for 1 hour. The mixture was basified by addition of saturated aqueous sodium carbonate solution. The organic layer was washed with brine, dried over magnesium sulphate and the solvent removed in vacuo to yield 7-benzyloxy-1-[1-(2-chlorophenyl)cyclopropyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline as a gum (0.42 g). This product was shown to have a 92% enantiomeric excess of one of the enantiomers.

Workup

  1. customto reach ambient temperature
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-96a5fc84d3bd4396b742c0314ab70506
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

Loading…