Potassium sodium tartarate → HCID 22127035, compound

HRID 1858708Notes

Reaction equation

HRID 1858708 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][CH2:16][N:15](C(OCC2C=CC=CC=2)=O)[CH2:14]1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1.C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][CH:13]1[CH:18]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

5

Reactant 2

HCID 9855836Potassium sodium tartarateHCID 54222315HCID 54222315, compound

Product 1

HCID 22127035HCID 22127035, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

30 mg, 0.065 mmol) of benzyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-phenoxy-piperidine-1-carboxylate were dissolved in 1.6 ml of tetrahydrofuran, cooled to 0° C. and treated in succession within 25 minutes with a solution of 95 ml (0.32 mmol, approximately 5 eq.) of a 70% sodium dihydrido-bis-(2-methoxyethoxy)-aluminate solution (SDMA) in toluene and 1.6 ml of tetrahydrofuran. This reaction solution was stirred at 0° C. for 2.5 hours. Subsequently, it was poured into a mixture of saturated potassium sodium tartrate solution and ice and extracted four times with 50 ml of methylene chloride each time. The organic phases were washed twice with water, evaporated under reduced pressure and dried in a high vacuum. The orange coloured resin was separated on silica gel using a 95:5 mixture of methylene chloride and methanol as the eluent. There were obtained 10 mg (47% of theory) of (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-phenoxy-piperidine as a colourless, amorphous solid; Rf : 0.38 (SiO2, methylene chloride:methanol=9:1).

Workup

  1. extractionextracted four times with 50 ml of methylene chloride each time
  2. washThe organic phases were washed twice with water
  3. customevaporated under reduced pressure
  4. customdried in a high vacuum
  5. customwas separated on silica gel using
  6. additiona 95:5 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-fe3c6348bfa54c68b12cb4ef6db546ad
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

Loading…