Triphenylphosphine → tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

HRID 1993869Notes

Reaction equation

HRID 1993869 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1C=CC(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:60]=[N+:61]=[N-:62])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 216370811,1-Dimethylethyl N-((1S,3R)-3-hydroxycyclopentyl)carbamate

Product 1

HCID 86608905tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamateYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of cis-(3-hydroxy-cyclopentyl)-carbamic acid tert-butyl ester (850 mg, 4.22 mmol) and triphenylphosphine (1.53 g, 5.83 mmol) in THF (25 mL) cooled to 2° C. was added DEAD reagent (0.92 mL, 5.84 mol) over 5 minutes. The mixture was stirred for 5 minutes and DPPA (1.26 mL, 5.84 mmol) was added over 5 minutes. Stirring was continued for 17 hours at room temperature. The mixture was evaporated to dryness. The residue was stirred in ethyl ether briefly and the white solid triphenylphosphine oxide was removed by filtration (1 g). The filtrate was again reduced in volume and purified by silica gel chromatography eluting with ethyl acetate and hexanes to afford trans-(3-azido-cyclopentyl)-carbamic acid tert-butyl ester (950 mg).

Workup

  1. stirringStirring
  2. waitwas continued for 17 hours at room temperature
  3. customThe mixture was evaporated to dryness
  4. stirringThe residue was stirred in ethyl ether briefly
  5. customthe white solid triphenylphosphine oxide was removed by filtration (1 g)
  6. custompurified by silica gel chromatography
  7. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-f52356fcfcfb4d849e7c019e6601a4d6
Source dataset
uspto-grants-2010_01
Patent number
US07652053B2

Reaction notes

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