Water → 2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

HRID 1039053Notes

Reaction equation

HRID 1039053 reaction equation
[N:1]([CH2:4][CH2:5][C@@H:6]1[CH2:8][C@@H:7]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:21][C:18]1[CH:17]=[N:16][C:15]([N:12]2[CH2:13][CH2:14][CH:9]([C@H:7]3[CH2:8][C@H:6]3[CH2:5][CH2:4][NH2:1])[CH2:10][CH2:11]2)=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86666142HCID 86666142, compound

Product 1

HCID 677784742-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{4-[(1S,2S)-2-(2-azidoethyl)cyclopropyl]piperidin-1-yl}-5-chloropyrimidine (34 mg, 0.11 mmol) from step 2 of this example was dissolved in THF (1 mL), triphenylphosphine (58.1 mg, 0.22 mmol) was added, then water (0.085 mL). The reaction was run at room temperature for 1 hour, then 40° C. 1 hour. The reaction was cooled down to room temperature, concentrated to dryness and purified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge eluting with 10% methanol/dichloromethane to give the title compound as a white solid.

Workup

  1. custom40° C
  2. custom1 hour
  3. concentrationconcentrated to dryness
  4. custompurified by column chromatography through a 12 gram RediSep Rf™ silica gel cartridge
  5. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-707de8f4b4514a0c84205a53f7702a99
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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