Water → HCID 69799484, compound

HRID 2179945Notes

Reaction equation

HRID 2179945 reaction equation
[N:1]([CH2:4][CH2:5][C@@H:6]([O:13][C:14]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48]>O1CCCC1.C(O)C>[C:46]([OH:51])(=[O:50])[C:47]([OH:49])=[O:48].[NH2:1][CH2:4][CH2:5][C@@H:6]([O:13][C:14]1[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 11776TriphenylphosphineHCID 86759692HCID 86759692, compound

Product 1

HCID 69799484HCID 69799484, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[[(1R)-3-azido-1-phenylpropyl]oxy]-4-(trifluoromethyl)benzonitrile (7.70 mg, 2.2 mmol) in tetrahydrofuran (50 ml) was treated with triphenylphosphine (1.5 eq.) and water (0.5 ml). The mixture was stirred at ambient temperature for 24 h then concentrated to an oil. The crude amine was purified on silica gel eluting with ethyl acetate, then 10% 7N ammonia in methanol/dichloromethane. The oil obtained was converted into an oxalate salt using 1 equivalent of oxalic acid in ethanol to afford the title compound as a colourless solid (510 mg, 56%).

Workup

  1. concentrationthen concentrated to an oil
  2. customThe crude amine was purified on silica gel eluting with ethyl acetate
  3. customThe oil obtained

Sources & evidence

ORD record
ord-e55d2037fd1e4c988079c2c834ea3f1d
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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