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Diethyl Ether → (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butylester

HRID 1531479
Notes
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Reaction equation

HRID 1531479 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH:40]=[CH:41][CH:42]=[N:43]3)=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+].CCOCC>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:18][CH:19]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][NH:43]3)=[CH:38][CH:37]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57033058(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(quinolin-7-yl-methoxy)-piperidine-1-carboxylic acid tert-butylester

Product 1

HCID 57314360(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butylester
Yield 77%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3.77 g (6.15 mmol) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(quinolin-7-yl-methoxy)-piperidin-1-carboxylic acid tert-butyl ester and 0.73 g (3.08 mmol, 0.5 equiv.) of nickel(II) chloride hexahydrate were dissolved in 50 ml of methanol. 0.93 g (24.8 mmol) of sodium borohydride was added at 0° C. in small portions over a period of 30 minutes. The resulting black suspension was then stirred for 1 hour at 0° C., and 2 hours at room temperature. The reaction mixture was slowly poured into a vigorously stirred mixture of 150 ml 5% ammonium chloride solution and 400 ml of ether. After further stirring for 30 minutes, the organic phase was separated. The slightly blue aqueous phase was further extracted 5 times with 50 ml of ether. The combined organic phases were washed twice with distilled water, then dried over magnesium sulphate, filtered and concentrated. The crude product (3.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 1:1 to yield 2.92 g (4.73 mmol, 77.0% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(1,2,3,4-tetrahydro-quinolin-7-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil; MS: 617 (M+H)+.

Workup

  1. custom2 hours
  2. customat room temperature
  3. stirringAfter further stirring for 30 minutes
  4. customthe organic phase was separated
  5. extractionThe slightly blue aqueous phase was further extracted 5 times with 50 ml of ether
  6. washThe combined organic phases were washed twice with distilled water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product (3.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-58a2173a1a8242cab6470bf99bff207d
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197959B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes