HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triphenylphosphine → (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

HRID 2233375
Notes
Print preview

Reaction equation

HRID 2233375 reaction equation
[N:1]([CH2:4][C@@H:5]([OH:22])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9][CH2:8]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:1][CH2:4][C@@H:5]([OH:22])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 59295965(2S)-1-azido-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol

Product 1

HCID 11151315(2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The resulting oil from Step 2 was dissolved in wet tetrahydrofuran (225 ml) and was treated with triphenylphosphine (53.3 g, 203 mmol). The reaction was heated at 60° C. and stirred for 4 h. The solvent was removed under vacuum, the residue re-dissolved into 2N hydrochloric acid (1000 ml) and the aqueous layer was extracted with ethyl acetate (3 times 700 ml). The aqueous phase was basified with a 2N sodium hydroxide solution and extracted with dichloromethane (3 times 1000 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under vacuum. The crude material was purified by chromatography (8% 7N ammonia in methanol/DCM) to give the title compound as a yellow oil (17 g).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue re-dissolved into 2N hydrochloric acid (1000 ml)
  3. extractionthe aqueous layer was extracted with ethyl acetate (3 times 700 ml)
  4. extractionextracted with dichloromethane (3 times 1000 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude material was purified by chromatography (8% 7N ammonia in methanol/DCM)

Sources & evidence

ORD record
ord-cc325a14caea47a3b72c208e9651f338
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709500B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes