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

HRID 2421012
Notes
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Reaction equation

HRID 2421012 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 oil from Step 2 was dissolved in wet tetrahydrofuran (225 mL) and was treated with triphenylphosphine (53.3 g). The reaction was heated at 60° C. and stirred for 4 h. The solvent was removed under vacuum, the residue redissolved into 2N hydrochloric acid (1 L) and the aqueous layer was extracted with ethyl acetate (3×700 mL). The aqueous phase was basified with aqueous 2 N sodium hydroxide solution and extracted with DCM (3×1 L). 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 redissolved into 2N hydrochloric acid (1 L)
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×700 mL)
  4. extractionextracted with DCM (3×1 L)
  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-bd6f2005c6d64a60a5bec0b6a64cb27d
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07956070B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes